THE PORPHYRINS Volume I

Structure and Synthesis, Part A

Edited by

DAVID DOLPHIN Department of Chemistry

University of British Columbia Vancouver, British Columbia, Canada

A C A D E M I C P R E S S New York San Francisco London

A Subsidiary of Harcourt Brace Jovanovich, Publishers

Contents

1 Nomenclature

R. BONNETT

I. Introduction 2 II. Pyrroles 2

III. Systems with Two Pyrrole Rings 3 IV. Porphyrins and Related Compounds: The Fischer Nomenclature 4 V. Porphyrins and Related Compounds: A Revised Nomenclature 9

VI. Linear Tri- and Tetrapyrroles 14 VII. Ring-Contracted and Ring-Expanded Systems 19

VIII. Metal Complexes 21 References 26

2 Selected Landmarks in the History of Porphyrins and Their Biologically Functional Derivatives

DAVID L. DRABKIN

I- Challenge of Disease States 31 II. Thudichum's Cruentine (Hematoporphyrin) 34

III. Experimental Disease States 36

IV. Important Books, Monographs, and Reviews 38 V. Conferences, Symposia, and Colloquia 40

VI. Determination of Iron Content of Hemoglobin (A Standard for Hemoglobinometry) 52

VII. Crystallization of Porphyrins, Hemes, and Hemoproteins 55 VIII. Hemochromogens 55

IX. Continuum of Concepts 61

X. Ongoing Problems: Return to the Functional Environment of the Cell 69

XI. Concluding Remarks 69 XII. Addendum 71

References 71

3 Synthesis of Porphyrins from Monopyrroles

JEAN B. KIM, A L A N D. ADLER, AND FREDERICK R. LONGO

I. Synthesis of Porphin and Chlorin 85 II. Synthesis of b-Substituted Porphyrins 87

III. Synthesis of meso-Substituted Porphyrins 88 IV. Mechanistic Considerations 90 V. Cis, Trans-Dipyrrylmethene and Polypyrrylmethene Precursors 95

VI. Substituent Effects 96 VII. Cyclic Tetrapyrrole Intermediates 97

VIII. Conclusion 99 References 99

4 Synthesis of Pyrroles and of Porphyrins via Single-Step Coupling of Dipyrrolic Intermediates

JOHN B. PAINE III

I. Synthesis of Pyrroles from Acyclic Precursors 101 II. Manipulations of Monopyrrolic Porphyrin Precursors:

Transformation of a-Substituents of 5-Methylpyrrole-2-Carboxylic Esters 135

III. Synthesis of Dipyrrolic Intermediates and Their Conversion to Porphyrins 163

IV. Appendix: Selected Examples of 2 + 2 Porphyrin Syntheses 224 References 231

5 Synthesis of Porphyrins from 1,19-Dideoxybiladienes-ac and 1,19-Dideoxybilenes-A

A. W. JOHNSON

I. Introduction 235 II. Linear Tetrapyrroles 237

References 263

6 Synthesis of Porphyrins from Oxobilane Intermediates

P. S. CLEZY AND A. H. JACKSON

I. Introduction 265 II. Dipyrroketones 266

III. Porphyrins from a-Oxobilanes 269 IV. Porphyrins from b-Oxobilanes 274 V. Differential Protection of Pyrrole Rings 279

VI. Synthesis of Porphyrins Bearing Labile Groups 280 VII. Conclusions 284

References 286

7 Isolation and Modification of Natural Porphyrins

ROBERT K. DINELLO AND C. K. CHANG

I. Introduction 290 II. Protoporphyrin and Related Natural Porphyrin Derivatives 290

III. Porphyrins Derived from Degradation of Chlorophylls 324 IV. Interconversion of Porphyrins by Chemical Means 329

References 334

8 N-Substituted Porphyrins and Corroles

A . H . JACKSON

I. N-Substituted Octaalkylporphyrins 341 II. N-Methylated Octaethylchlorins 352

III. N-Alkyl-meso-Tetraphenylporphyrins 354 IV. N-AIkylcorroles 357 V. N-Acetylcorroles 361

VI. Conclusions 362 References 363

9 Azaporphyrins

A. H. JACKSON

I. Introduction 365 II. Monoazaporphyrins 365

III. Diazaporphyrins 369 IV. Tetraazaporphyrins (Porphyrazines) 370 V. Phthalocyanines 374

VI . Analogues of the Phthalocyanines 380 VII. Mono-, Di-, and Triazabenzoporphyrins Related to

Phthalocyanines 383 References 387

10 Synthesis and Properties of Metalloporphyrins

JOHANN WALTER BUCHLER

I. Introduction 390 II. General Considerations 395

III. Central Metals of Group la (Alkali Metals) 424 IV. Central Metals of Groups Ha and l ib (Alkaline Earth and Zinc

Metals) 425 V. Central Metals of Groups Ilia, Illb, and the Lanthanoids 428

VI . Central Metals of Groups IVa, IVb, Va, and Vb 432 VII. Central Metals of Groups Via and V i l a 440

VIII. Central Metals of Groups V i l l a and lb 447 IX. Postscript 474

References 474

11 Geochemistry of Porphyrins

EARL W. BAKER AND SUSAN E. PALMER

I. Introduction 486 II. Isolation and Fractionation of Geoporphyrins 488

III. Identification Methods 493 IV. Treibs' Scheme 505 V. A Survey of Geoporphyrins: Occurrence and Properties 511

VI . Diagenetic Reactions of Tetrapyrroles 536 VII. Concluding Remarks 545

References 550

12 Chromatography of Porphyrins and Metalloporphyrins

WILLIAM I. WHITE, ROBERT C. BACHMANN, AND BRUCE F. BURNHAM

I. Introduction 553 II. Porphyrins and Metalloporphyrins 559

III. Porphyrin and Metalloporphyrin Esters 565 IV. Synthetic Porphyrins 569 V. Conclusion 574

VI. Addendum 574 References 576

13 Nonchromatographic Methods of Purification of Porphyrins

VERONICA VARADI, FREDERICK R. LONGO, AND A L A N D. ADLER

I. Introduction II. Electrophoresis

581 584

III. Countercurrent Distribution 584 IV. Extraction Methods 584 V. Precipitation and Crystallization 585

VI. Sublimation 586 VII. Miscellaneous 587

VIII. Problems and Future Perspectives 588 References 588

Contributors

A L A N D . A D L E R

ROBERT C . B A C H M A N N

E A R L W . B A K E R

R . B O N N E T T

J O H A N N W A L T E R B U C H L E R

B R U C E F . B U R N H A M

C . K . C H A N G

P . S . C L E Z Y

ROBERT K . D I N E L L O

D A V I D L . D R A B K I N

A . H . JACKSON

A . W . JOHNSON

J E A N B . K I M

F R E D E R I C K R . L O N G O

J O H N B . P A I N E III

S U S A N E . P A L M E R

V E R O N I C A V A R A D I

W I L L I A M I . W H I T E

Author Index

Numbers in parentheses are reference numbers and indicate that an author's work is referred to although his name is not cited in the text. Numbers in italics show the page on which the complete reference is listed.

A

Abd-Elmageed, M. E . , 468(265, 278), 469(265),482, 483

Abeysekera, A. M . , 346( 14b),363 Abraham, R. J . , 345(13),363, 421(112),

429(112), 430(112), 431(112, 113), 437(112), 472(282),478,483

Adair , G S , 41, 45(149), 76 Adkins , H . , 108(21),231 Adler , A D , 41, 45, 51( 145, 256), 52(145)

76, 87, 89, 92, 94, 95(6, 41, 42), 96, 97(6), 98,99, 100, 408(49), 424(49), 440(49), 441(49),476 498(22),550, 562(33), 569(104), 572(123, 124, 129, 104)572, 579

Ahmadi , A . , 58(355), 60,52 Ahrland, S., 432(121), 438( 121),478 Akesson, A . , 46(154), 58(350), 60, 76,

309(63), 336 Alben , J. O. 291(6), 292(6), 294(6), 295(6),

296(6), 298(6), 299(6), 300(6), 301(6), 302(6), 303(6), 334, 440(172), 447(172), 449( 172), 450( 172), 454( 172), 458( 172), 459(172), 460(172),479, 568(93,96)575

Alexander, L. E . , 486(7a), 550 Alexander, W. A . , 377(47),388 A l - H a z i m i , H. M . , 354(26), 355(26), 260(26),

364 Al len , D. W . , 64(372), 69(372),82

Al l i son , J. B . , 416(67, 69), 424(99), 425(67), 426(67), 447(67, 99), 449(69),476, 477

Almong, J . , 450(200, 201), 454(200, 201), 455(200, 201),480

Al tu rk i , Y I A , 488( 14), 490(14), 502(25), 503(28, 25), 515( 14, 38), 520(25), 521(25), 522(25), 542(38), 550, 551

Amoroso, E . C . , 32(49), 73 Amundsen, A. R . , 454(225),481 Anderson, B. F . , 357(30),364 Anderson, D. L . , 450(197), 454(197),

455(197), 457(235), 465(197), 466( 197), 480,481

Anderson, O. P . , 356(26b),364 Andrews, J. E . , 538(51), 551 Andrews, J S , 37, 74 Angstroo, A. J . , 40, 74 Anson , M. L . , 57, 58(323, 324, 344), 59,81 Antipas, A . , 465( 260), 466(260), 482 Anton, J . A . , 89,100 Antonini , E . , 39, 40( 109a), 74, 392(8),

450(8), 454(8), 455(8), 465(8), 466(8), 475

Appleby, C. A . , 42(214), 78 Arellano, R. , 571(116).579 Aronoff, S , 89, 96( 18, 19), 97, 99, 327( 158),

329, 503(30), 550, 572(119, 120), 579 Arno ld , Z, 135(58),232 Arnone, A . , 44( 168), 47, 48(168), 68, 76 Arsenault, G. P., 177(91), 179(91), 184(91),

224(91), 225(91),233, 236(5), 263,

273(28), 283(28),287, 319(119).337 Asahina, Y . , 32(60), 73 Asakura , T . , 302(43), 303(49), 305(49),

306(49), 313(43), 335, 562(43a), 563(49), 577

Assour, J . , 89(34), /00, 572( 124),579 Aust in , J. H . , 30(14), 34(14), 49(182),

54(302), 55(284, 302), 56, 58(302), 59, 72, 77,80

A x e l r o d , L R , 556(12), 576 Ayer , W. A . , 8(7b), 236(b), 238(6), 263,

281(6), 287

B

Bachmann, R. C . , 292(8), 320(8), J J < 554(5) 567(5), 576

Bacon, R. F . , 114(28), 231 B a d e r , R . G . , 538(50),551 Badger, G. M . , 87, 89, 90(8), 90, 91, 94, 97,

99, 100, 153, 154(75), 155(75), 156(79), 233, 240, 249, 256(15), 259( 15), 263, 568(92), 572(118), 578, 579

B a g u l e y , M . E . , 370(14),387 Bailey, W. A . , Jr., 156(80), 160(80), 169(80),

233 Baker, B. L . , 44(274), 51(274), 52(274), 79,

80 Baker, E. W . , 44(247), 51(247), 79, 299(38),

300(39), 331,335, 345( 11),363 486(5), 488(11, 20), 490(11), 491(20), 494(6), 499(24), 502(5), 509(6, 50), 513(35), 514(36, 37), 517(11), 518(6, 40), 520(6, 24, 40), 521(24), 522(43), 528(5), 535(24), 538(50), 538(52), 542(6), 543(24), 544(24), 550, 55J, 568(90), 578

Baldas, J.,322(143),338 Baldwin, J. E . , 450(200, 201), 454(200, 201),

455(200, 201), Balek, R. W . , 571(117), 579 B a l l , R . H . , 89(19), 96(19), 99, 572(120),579 Ballantine, J. A . , 148(69), 165(69), 218(69),

220(69), 233, 267'(12), 268( 12), 269( 12), 271(12), 286

Baltazzi , E . , 169(87), 224(87), 225(87),233, 265(3), 271(3), 286, 319(120),337

Bamfie ld ,P . , 151(73), 187(95), 205(95), 207(73), 208(105),2J5, 234, 242(23), 243(23, 25), 244(25), 261(23), 262(23,

25), 263, 304, 305(53), 321(53), 327(162), 329(162), 335,339

Baptista de Almeida, J. A. P. , ll9(32a),2J/ Barbuto, J . , 576(145),580 Barcroft, J . , 39,40(124), 57(324), 58(324),

59,75, 81 Bardachz i ,F . , 58(339), 59,8/ Bardos, T. J . , 89,100, 459(245), 468(270),

469(270),482, 572(121),579 B a r k a n , G . , 54, 55(301),80 Barlow, C. H . , 450(193, 204), 451(193, 194),

453(193, 194), 454(193, 194,204), 457(204), 458(193), 461(194), 462( 193), 480

Barnes, H. D . , 321(134),338 Barnes, J. W . , 424(102),477 Barnett, G. H . , 421(112), 429(112), 430(112),

431 (112), 437( 112),478, 572( 128),579 Barrett, J . , 42, 77, 293(16), 298(31), 299(31),

310(75), 311(75, 78, 80. 82), 313(31,99, 101),334, 336, 337, 564(62), 578

Barrett, P. A . , 376(42), 377(44,45), 384(65, 66), 386(65, 66), 388

Barron, E. S. G . , 44(267), 51(267), 79 B a r t h , G . , 423(98), 477 Bartozah,T. J . , 357(30),364 Basolo, F . , 443(149), 450(197), 454(197),

455(197), 457(235, 237), 465(197), 466(197), 468(237), 479, 480,481,482

Batten, P . , 350(20),364 Battersby, A. R . , 111(23, 24), 121(33),

124(24), 125(23,24), 135(59), 141(59), 153(24), 154(24), 155(77), 160(24), 163(77), 169(59), 172(24), 180(24), 224(24), 225(24), 231, 232, 233, 244(33), 248(33), 260(33), 262(33),264, 320(126), 322, 329,338, 339 574(140), 576(140), 580

Baum, S. J.,406(44),476, 569(103),579 Baumann ,F . , 265(1), 286 Baumle r ,R . , 44, 51(250), 79 Bayer, E . , 451(220, 221), 454(220, 2211481 Bearden, A. J . , 292( 10),334,423(93),

424(94), 459(93), 461(93), 477 Beam, A . G . , 30, 42(23), 45(23), 46(23),72 Beaton, J. M . , 8(7b), 26 , 236(6), 238(6),263,

281(34), 287 Beaudreau, C. A . , 440(172), 447(172),

449(172), 450(172), 454(172), 458(172), 459(172), 460(172),479, 568(96),578

Becker, E . , 298(29),335

Becker. R. S., 416(67, 69), 424(99), 425(67), 426(67), 447(67, 99), 449(69), 476, 477

Beetlestone, J . , 42( 186), 47(167), 49(186), 66(167), 67(167), 76, 77

Beitchmund, P . , 86, 99 Belcher, R. V . , 283(43), 284(43),288,

561(29), 563(52), 564(52),577 Benesch.R.. 48, 61(171), 76 Benesch.R. E . , 48(171), 61(171), 76 Benson. A . , 292(9),334, 565(71,73,74),

566(74). 578 Ben von. J. H . , 378(49), 388 Berg. H . , 235(2), 263, 299(35),335 Berg. M. H . , 556( 15), 561(27a),577 Bernhart. F. W . , 54, 55(296), £0 Bernstein, S. H . , 61, 62(365),82 Bertin-Sans, H . , 57, 58(325), 59 ,5 / Berzelius, J J , 38, 74 Bessis, M. C , 64, 69(373),82 Beznak. M . , 46(154), 76 Bhatti, M . , 410(62), 429(62), 476,572(122),

579 Bhatti. W. , 410(62), 429(62),476, 572(122),

579 Bickelhaupt, F. ,8(7b),26, 236(6), 238(6),

263, 281(34),287 Billig, M J , 488(20), 491(20), 550 Bilton, J. A . , 381(58),388 Birkhofer, L . , 64(379), 69(379),82 Bischoff H , 58(342), 59 8/ Biswas, K M ,267(12a, 12b), 268( 12a, 12b),

269(l2a, 12b),271(12a, 12b), 286 Blaud, P , 31(33), 72 Bliesener, K. M . , 293(17, 18), 302(45),

304( 17,18), 305(18), 306(18), 307(18), 335, 568(94), 578

Blomer, O. , 32(59), 62(59), 73 Bloomfield, B . , 298(30), 299(30), 313(96),

335, 337 Blum, H F , 32(43), 72 Blumer, ML, 487(8), 488(16), 489(16),

491( 16). 499(8). 528(5), 533(8), 533( 16), 534(8), 541(56), 545(8), 546(64), 550, 551, 556(9), 567(88), 576, 578

Bock H ,293(15),JJ4 Bodansky, O. , 31(31), 72 Bodo,G , 55(318), 56,81 Boeri, E , 42(213), 78 Bogorad, L . , 36(87), 37(91), 42(87), 45,

48(87), 74, 317(110),J57, 565(69,72), 568(72), 578

Bohr, C, 47(164), 76 Bollinger, K . M . , 129(46),232 Bommer, J . , 576(145),550 Bonner, W. D . , Jr., 43, 50(242), 78 Bonnett, J. J . , 447( 167), 448( 167),465(167),

466(167), 479 Bonnett, R . , 2(2, 3), 8(7b),26, 43(264),

51(264), 79, 236(6), 238(6), 263, 269(24), 281(34), 287, 410(60), 440(174), 447(60, 174), 449(60, 174), 450(174, 208), 454( 174, 208), 466( 174), 476, 479, 481, 501(60), 543(60), 544(60),551, 570(111), 579

Bonnichsen, R. , 46(154), 76 Booth, G . , 374(29), 375(29), 377(29),

379(29), 387 Borg, D. C, 9(13), 26, 43, 51(259, 260), 79,

462(258), 482 B o r s o o k , H , 42, 77 Bossenmaier, I., 299(35),335, 556(15),

561(27a), 566(76), 568(76), 577, 578 Boucher, L. J . , 19(24),26, 442(143),

443(148), 444(143),479, 533(46), 534(46),557, 568(98), 569(99),579

Bower, B. K . , 410(61), 421(61), 427(61), 447(61), 449(61), 468(271), 470(271), 476,483

Bowman, R. G . , 457(235),481 B o y d , P , 573(132),579 B o y e r , F . , 125(42), 147(42), 232 Boylan, D. B . , 432(123), 433(123), 437(123),

478, 488( 19), 491 (19), 492( 19), 502(26), 503(19, 28), 505(19), 550

Boyle , R , 70(387), 82 Bradbrook, E. F . , 376(42), 381(57),388 Bradley, R . , 298(29),335 Brainerd, F. A . , 30(17), 45(147), 72 Brault, D.,454(225a),4S/ B r a u m a n J . E, 457(232, 232a),481 Braun, A . , 374(32).388 Brauni tzer ,G. ,30,40(109d, 136), 67, 72 , 74,

75 Breger, I. A . , 544(62),551 Brewer, P. , 501(60), 543(60),55/ Brewster, D . , 70(389),83 Brinigar, W. S., 450(203), 454(203),

455(203), 459(241), 480, 482 Broadhurst, M . J . R . , 21(28), 26, 241(19),

246(19), 256(29), 346(16), 357( 16, 29), 358(29), 360(16), 361(29),363

Brockmann, H . , Jr., 88(13), 99, 293(17, 18),

302(45), 304(17, 18), 305(18), 306(18), 307(18), 333(44), 334, 335, 336, 421(184), 447(184), 449( 184), 480, 554(10), 568(94), 576,578

Broomfield, S. N . , 375(40),388 Brown, A. P. , 55(310), 70(310),80 Brown, E. B . , 64, 69(374),82 Brown, G. M . , 423(92), 447(92, 164), 448(92,

164), 452(92), 464(92, 164), 465( 164), 477, 479

Brown. H. C, 268( 18), 271(25), 287 Brown , P . M . , 370(\6),387 Brown, S. B . , 454(21 lb),481 B r u c k , S D , 457(233),45/ Brunori , M . , 392(8), 450(8), 454(8), 455(8),

465(8), 466(8), 475 Bubnova, A. G . , 244(29), 262(29),263 B i i c h e r , T \ , 69(383),82 Buchler, J . W . , 43(253-255), 51(253-255),

79, 392(2, 9), 393(2), 395(2, 19), 397(19, 23, 24, 25), 398( 19, 24, 25), 400( 19, 24), 403(23, 39), 404(40), 407(2, 19, 23, 40, 46), 408(2, 48), 409(2, 9), 410(2, 19, 23, 59), 411(2, 19, 23, 39), 414(2), 415(66), 416(48, 66), 417(2, 19, 66, 74), 418(2, 19, 74) , 419(75), 420(19, 48, 77), 421( 19, 39, 78), 422(2, 23, 24, 25, 39, 83, 84), 423(23-25, 39, 40. 84, 89), 425(43, 107), 426(42, 107), 427(19, 42, 148), 429(19, 23, 39, 46, 75, 118, 119), 430(23, 39, 46, 75) , 430( 19, 23, 40, 46, 75), 432(2, 23, 24, 25, 39, 40, 46, 48, 127), 433(23, 24, 25, 39,40,48), 434(2, 23, 24, 46, 127), 435(2, 23, 39), 436( 19, 23, 24, 25, 40, 46), 437(39, 119, 127), 438(23, 24, 25, 40), 439( 12, 75, 127), 440( 19, 23, 24, 25, 39,40, 136), 441(19, 23,24, 136), 442(19, 24, 39) 444( 19, 24, 39, 75, 157), 445(39), 446( 19, 23, 39, 157, 158), 447(2, 42, 48, 59, 75, 78, 83, 84, 89, 170), 449(2, 42,48, 59,75, 170), 450(90), 451(75, 214), 452(77, 78, 83, 84, 89, 170), 453(2, 75, 190), 454(212, 214,), 456(2, 75), 458(84, 190), 459(2, 75, 190), 460(75, 190,212), 461(214), 462(19, 158, 190), 464(78, 83, 84), 464( 170), 465(77, 83, 84, 89, 170, 260), 466(77, 83, 84, 89, 170, 260), 467(77, 84), 468(84), 472(2, 19), 473(19, 118, 119, 158), 474(19, 42), 474, 475,

476, 477, 478, 479, 480, 481, 482, 570(12), 572(112), 579

Buchschacher, P . , 8(7b),26, 236(6), 238(6), 263, 281(34),287

Buckley, D. G . , 574(140), 576(140),580 B u d z i k i e w i e z , H , 422(79),477 B u l l , C , 443(150),479 Bullard, L . , 251(215), 454(215), 262(215),

481 Bullock, E . , 104(5), 122(5), 123(5), 126(5),

127(5), 177(91), 179(91), 184(91), 224(91, 114), 225(91, 114),23/, 233, 236(4,5), 250(46),263, 264, 269(20), 273(28), 283(28),287, 310(72), 319( 119),336, 337

Bunnenberg, E . , 44(275), 51(275), 52(275), 79, 80, 423(98),477

Burbidge, P. A . , 541(57),551, 566(79), 570(79), 578

Burger, H . , 422(82), 423(82), 477, 568(19), 578

Burke, J . M . , 423(85),477 Burnham, B. F . , 292, 320(8),334, 406(44),

476 , 554(5), 567(5), 576(145), 576, 580 Burns, R. E . , 538(51),557 B u r w e l l , R . L . , Jr., 457(235),481 Butterfield, E. E . , 53, 55(291),80 Bybnova, A. G . , 244(32),264 Byrne, G. T . , 374(34), 375(34), 377(34),388

C

Caiger, P . , 298(30), 299(30),335 Cajori, F. A . , 30(17), 45(17), 72 Calaveiro, J. A. S., 277(3la), 278(3la, 54,

55), 281(6, 31a)2S7, 288 Calderazzo, F . , 409(51),476 Callot, H. J . , 351(21, 22), 356(23, 27),

357(27), 364 Calvert , C. R . , 565(70),578 Calv in , M , 89, 96(18, 19), 97,99, 100,

432(123), 433(123), 437(123), 443(146, 15\),478, 479, 486(2), 488(19), 491(19),

492(19), 503(19), 505(19), 539(2),550, 572(119, 120),579

Campbell , D. S., 147(68),233 Cannon, R. K . , 52(283), 54(288),£0

Caputo, A . , 39, 40( 109a), 74 Cardinal, R. A . , 566(76), 568(76),578 Carlson. E . G . ,498(22), 550 Carlson, R. E . , 3 18( 114),337, 574(136, 138),

575(136), 576(138),579, 580 Carlton, J . K . , 570(108),579 Carr ,R . P. , 121(34), 217(108),232, 234,

244(34), 257(34), 260(34),264, 275(38), 278(38), 282(38), 284(38), 287, 288, 292, 334

Carrol, F. A . , 439( 134),478 Cartwright, C. E . , 41, 44, 46(142), 76 Casagrande, D. J . , 501(32), 503(32), 520(32),

522(32), 550 Castro, A. J . , 108(19),231 Caughey, W. S., 43, 44, 50(221, 224, 225),

51(266), 67(221),7S, 79, 291,292, 294(6), 295, 296(6), 298(6), 299(6), 300(6), 301(6), 302(6), 303(6), 309(71), 311(71), 312(71), 313(100, 102), 3 15(71, 100), 316(71),354, 335, 336, 337, 342(3), 346(3), 347(3), 363, 440( 172), 447( 172), 449(172), 450(172, 192, 193,204), 451(192, 193, 194, 217a), 453(192, 193, 194), 454(172, 192-194, 204, 217a), 456(231), 457(204), 458(172, 192, 193), 459(172, 192, 242, 243), 460(172, 192). 461(192, 194), 462(192), 465(192), 466( 192, 193), 472(283),479, 480, 481, 482, 483, 564(65), 568(93, 96, 97),578, 579

Cavaleiro, J. A. S., 107(13), 161(81), 170(81), 179(92),231,233, 265(6), 281(41). 285(53-55), 286, 288

Caventou, J. B . ,38 ,74 Cazeneuve, P . , 38,40(120), 75 Cekan,Z. , 556(11),576 Cerchez, V . , 107(17),231 Chance, B . , 30, 41, 42, 43, 45( 17), 50(233),

55(233), 56, 72, 76, 78 Chang. C. C, 423(86), 450(86), 454(86),477 Chang, C. K . , 327(160, 161),329, 450(203),

454(203, 226), 455(203), 458(226), 459(241), 480, 481,48J

Changeux, J .-P. , 37(97a), 74 Chanutin, A . , 48, 61(170), 76 Chapman, D. J . , 19,26, 558(20),577 Charalambides, A. A . , 450(208), 454(208),

481

Charles, R. G . , 129(47), 130(47),232 Chatterjee, A . , 442( 142), 444( 142), 479 Chen, B. M. L . , 43(257), 51(257), 79 C h e n , M . F . , 107(16), 108(16),231 Cheng, D. O. , 88, 99 Cheung, S. K . , 440( 139), 441( 139),479 Chevrier, B . , 398(25a), 422(25a), 423(25a),

475 Chivvis , A. B . , 43(247), 44(272), 51(247,272),

79, 345(1 \)J63 Chong, R . , 126(43), 146(65), 179(65),

182(65), 224( 112), 225( 112), 232, 234, 268(17), 286

Chow, B C , 447( 165), 448( 165), 449( 165), 464( 165), 465( 165), 466(165), 468(275), 469(275), 471(275), 479, 483

C h o y , C . K . , 402(38), 474(38),475 Chu, E. J. FL, 145(63), 146(63),232,

318(113),337, 561(30), 562(38), 565(67, 68), 566(38, 75), 567(75, 85, 86, 87), 568(85, 86, 87),577, 578

C h u , T . C , 145(63), 146(63),232, 318(113), 337, 561(30), 562(38), 565(67, 68), 566(38, 75), 567(75, 85, 86, 87), 568(85, 86, 87),577, 578

Church, A H , 33, 75 Clack, D. W . , 377(46),388 Clark, B . A. J . , 135(58),232 Clark, L. F . , 499(24), 520(24), 521(24),

535(24), 543(24), 544(24),550 Clark, W. M . , 44(268), 51(268), 58(268, 334,

335, 349), 61, 79, 81 Clarke, D. A . , 242(21), 244(21), 246(21),

258(21), 261(21), 268(272), 269(272), 470(272), 263, 283

Clarke, J. A . , 367(7), 368(7),387 Clarke, T . , 43(227), 50(227), 78 Claude, A . , 30, 71 Cleave, H . , 58(358), 60(358),82 Cleve, FL, 58(356), 60,52 Clezy , P. S., 42, 77, 105(12), 126(43),

145(62), 145(64), 146(65, 66, 68a), 151, 169(86), 170(86), 175(64), 179, 182, 184, 185, 186(71), 195, 207(104), 215, 216(62), 218, 220(71), 221(71), 223, 224(90, 104, 109, 111, 112, 116, 117), 225(111, 112), 228(90, 104, 109, 116, 117). 229(116), 230(116),231, 232, 233, 234,240, 241(20), 244, 249(22), 251, 252,

253, 254(54), 255(42), 256, 258(16), 259(16, 42, 54), 265, 264, 265(5), 267(14), 268(17, 19), 269(19, 23), 278(32c), 280(32c), 281(33, 38a),286, 287, 288, 293(14), 298(31), 299(31), 307, 310(75), 311(75,78,82), 312,313(101. 334,335, 336, 568(95), 578

Closs, G. L . , 8(7b), 26, 236(6), 238(6),263, 281(34), 287

Codding, P. W . , 43(257), 51(257), 79 Cohen, I. A . , 402(37), 447( 165), 448( 165),

449( 165), 451(211), 454(211), 459(242, 244), 462(244), 463, 464( 165), 465( 165), 466(165), 468(275), 469(275), 471(275), 476,479,481,482,483

Cohn, E J , 31, 72 C o l e , R . D . , 42(177), 48(177), 77 Cole , W . J . , 19(23),26 Coll ier , G . , 541(57),551 Coll ier , G. L . , 281(37),288, 566(79), 578 Coll ins , D. M . , 425(106), 426(106),478 Coll ins , J . , 322(143),338 Collman, J. P . , 89(32), 100, 450(195, 196,

199, 205), 451(219), 453(191), 454(191, 195, 196, 199, 205, 219), 455(199), 456(199), 457(232, 232a), 458(205), 459( 196), 460(219), 465( 199), 466( 199), 468(267), 469(261),480, 481,482

Conant, J. B . , 39,40(126, 134), 42, 75, 77, 3 2 6 , 3 2 7 ( 1 5 5 ) , ^

Conlon, M . , 254(55), 264, 361 (32), 364 Connell , C. R . , 417(72), 432( 128b),

437(l28b), 476 Connelly, J. L . , 311(81), 313(92, 93), J J6 ,

337, 564(64), 578 Conrad, M. E . , 63, 69(370),80, 82 Conway, D C, 569( 102), 579 Cook, A. H . , 39, 40(128), 75, 373(22),387 C o o k s o n , G . H . , 36, 62(86), 74, 267(15),286 Coolidge, E . C , 237(10), 263 Cooper, D. Y.,43(243-245), 50(243-245),

78, 79 Conant, J . B . , 8 , 2 6 Connely, J . , 42(207), 78 Cope, B . T . , 25(31, 32), 27 Corey, R. B . , 30(18), 40( 138), 72, 75 Cornford, P . A. D . , 565(73),578 Corwin , A H , 9,26, 37, 39, 40( 129), 44,

51(247), 74, 75, 79, 107(18), 108(18), 124(40), 156(80), 160(80), 169(80), 199( 100), 202( 100), 204,231, 232, 233,

234, 237(10), 239,263, 299,300(39), 331(39),335, 343(6), 345(11), 347(17), 363, 419(76), 440(173), 447(173), 449( 173), 451(216), 454(216), 457(233), 459( 173),477, 479, 481, 486(4), 488(18), 489(18), 491( 18), 494(6), 509(6), 518(6), 520(6), 542(4, 6),550, 568(90), 569(106, 107), 571(116),578, 579

Corye l l , C. D . , 25(33), 27,49(183), 58(346), 59 ,77 ,3 /

Cotton, F. A.,416(18),418(18),439(18), 458(18), 474(18), 475

Cotton, V . , 321(138),338 Couch , P. W . , 278(44), 283(43, 44), 284(43),

285(43), 288 Coulson, A. F . W . , 298(33), 313(33),335,

563(50), 564(50), 567(50), 569(50), 577 C o x , M. T . , 257(62), 260(62),264, 278(45),

283(45, 45b), 284(45, 45b),288 C o y , U . , 43(223), 50(223), 78, 311(77, 83),

336 C r e s p i , H . L . , 19(24),26 Crook, P. J . , 115(30a), 116(30a), 162(82),

231, 233, 257(60), 260(60),264, 275(32), 278(32), 279(32), 284(52), 287, 288

Crosby, W. H . , 63, 69(370),82 Cullen, D. L . , 399(27), 408(27), 425(27),

440(27), 442(27), 446(27), 447(27),475 Cull is , A. F . , 68, 69(382),82 C u r n i s h , R . R . , 48, 61(170), 76

D

D ' A n d r e a , R . W . , 133(51),232 Dandridge, A. G . , 374(31),388 Danieli , G , 37(100), 42( 100), 46( 100), 74 Dannenberg, H . , 313(96),337 Darwin, C , 70(393),83 Das, R. R . , 573(135),579 Datta-Gupta, N . , 89(20), 100, 459(245),

468(270),469(270),482, 572(121), 572(127), 579

Davenport, H . , 309(60),336 Davidson, E. R . , 378(52),388 Davies, H . C , 43(238), 50(238), 78 Davies, J. L . , 195(98), 224(98), 226(98),234 Davies, T. H . , 58(335, 349), 6],81 Davis, D. G . , 423(91), 447(185), 449(185),

472(185), 473(185),477, 480 Davis, J. L . , 3 15(103),337 Dawson, P. J . , 367(7), 368(7),387 Day, R. O . , 442( 144),479 Day, V W , 442(144),479 Dean, R . T . , 576(144),580 Dearden, G. R . , 342(2), 345(2), 346( 15),

347(18), 348(2), 351(2),363, 364 Deasy, C. L . , 42( 174), 48( 174), 77 deC. Hinds, L . , 573(132),579 de Diesback, H . , 374(34),388 tie D u v e , C , 45(148), 76 D e F i l i p p i , L , J , 576(144),550 Degens, E. T . , 505(33), 513(33),550 Deilmann, K. O . , 55(314),50 del C. Battle, A. M . , 565(74), 566(74),578 D e l o r y , G . E . , 54, 55(300),80 Demole, E . , 566(77),578 Dent, C. E . , 375(38, 39), 376(42), 377(44),

384,386,355 Despuy, M. E . , 135(55),232 DeVaux, St. C y r , 58(356),82 D h e r e , C , 4 9 , 77 Diakiw, V . , 105(12),231, 252(51),264,

568(95), 578 Dicker, I. D . , 248(40),264 Diekerson,R. E. ,39,40(109c, 139),

44( 11 la), 51( 139), 67(139, 380), 69(380), 74, 75,82

Dickie, J. P . , 499(24), 520(24), 521(24), 533(46), 535(24), 543(24), 544(24),550, 551

Didyk, B . , 502(25), 503(25), 515(38), 520(25), 521(25), 522(25), 542(38),550, 551

Diebdd, T. , 398(25a), 422(25a), 423(25a),475 Dietz, E. M . , 326(155), 327(155),338 Dilcher, R. L . , 488(13),490(13), 501(13),

538(13), 550 Dilling, W , 58(338), 59,57 Dimsdale, M. J . , 269(24),287, 410(60),

440(174), 447(60, 174), 449(60, 174), 450( 174), 454( 174), 466( 174), 476, 479

Di Nello, R K , 564(66a), 578 Dinsmore ,H. , 299(35),335, 556(15),

561 (27a), 577 Dixon, F . L . , 471(281),483 Dixon, P F , 574(138, 139, 140, 142),

576(138, 139, 140, 142), 580 Dje ra s s i ,C , 423(98),477 D o a k , K . W . , 124(40), 199(100), 202( 100),

232, 234

D o h n , E . J . ,31,72 Dolphin, D . , 9( 13),26, 43, 51(259-261, 264),

79, 88( 15), 90(36), 91(35), 94, 97,99, 100, 193(96),233, 241(18), 246(35, 37), 263, 264, 306(55), 318(114),336, 337, 407(46), 421(46), 422( 125), 423(46), 429(46), 430(46), 431(46), 432(46, 125), 433(125), 434(46), 436(46), 437( 125), 450( 188a), 453( 188a), 454( 188a), 459(188a), 462(256-258), 463(256), 468(272), 469(272), 470, 473(287),476, 480,482,483, 564(66a), 572( 126), 574(138), 576( 138), 578, 579, 580

D o n n a y , G . , 535(49),551 D o r o u g h , G . D . , 89(20, 21), 99, 100, 416(68),

424(68, 102), 425(68), 427( 110), 447(68), 449(68), 453(68), 472( 110),476, 477, 478

Doss. M . , 554(4), 556(4), 567(81, 84), 568(91),576,575

Dougall , D. K . , 236(4),263, 310(72),336 Dougherty, R. C . , 19(24),26 D r a b k i n , D . L . , 29(1), 30(3, 13, 14), 31(1, 3,

25-30, 36), 32(36), 34( 14, 36), 35, 36(79), 37(28, 36), 39, 40(3, 13, 135), 41, 44,45(27,36. 135), 46(3, 27, 152), 47, 49(182, 187, 192, 195), 50(192, 195), 51(192), 52, 54, 55(135, 162, 163,284-286, 302,315,317), 56,57(329, 330, 331), 58(302, 330-333, 348, 351, 353, 354, 355), 59, 61(1, 3, 13, 25-30, 79), 62(3, 27, 28, 330), 63(3, 28), 64(3, 28, 367, 66(135), 68(367), 69(3, 28, 367), 70(324), 71, 72 , 73 , 75 , 76 , 77,80,82

Drescher, H . A . E . , 374(31),355 Dressel, E. I. B . , 292(9),334 Dunning, H. N . , 44(273), 51(273), 79,

505(34),550, 570(108),579 Dutler, H.,8(7b),26, 236(6), 238(6),263,

281(34), 257 Dwornick, E. J . , 535(47),551 Dyer, R. L . , 450(201), 454(201), 455(201),

480 D y m , S., 87, 95(6), 96(6), 97(6), 99 Dymock, K. R . , 451(217), 454(217),45/

E

Eaton, G. R. , 395(21), 429(21), 435(21), 439(21), 444(156), 447(21, 167, 168),

448(21, 167, 168),464(21),465(21, 167), 466(21, 167),475, 479

Eaton, S. S., 395(21), 429(21), 439(21), 447(21, 167, 168),448(21, 164, 168), 464(20,465(21, 167),466(21, 167), 475

Eaton, W. A . , 417(72), 435(21),476 Eberspaecher, H. I., 459(243).482 Edmonson, P. R . , 320( 128),338 Edsall , J T , 41, 44, 46(142), 76 Efron, M. L . , 67(381), 69(381),82 Eglinton, G . , 486(2), 448( 14), 490( 14),

502(25), 503(25, 28), 515( 14, 38), 520(25), 521(25), 522(25), 539(2), 542(38),550, 551

Ehrenberg, A . , 43, 50(236, 237), 78 Eikelmann, G . , 397(23), 403(23), 407(23),

410(23), 411(23), 422(23), 423(23), 429(23), 430(23), 431(23), 432(23), 433(23), 434(23), 435(23), 436(23). 438(23), 440(23), 441(23), 446(231 ),475

E i r i c h , F , 56(163), 76 Eisner, U . , 43(251), 51(251), 79, 87,88,

96(7), 97, 99, 267(15), 286, 407,410(57, 58). 425(47), 447(57, 58), 449(57, 58), 476

Elder, G. H . , 224( 113), 225(113),234, 280(32a),257, 318(112), J J7

Eley, D D , 378(49), 388 E l i x , J A , 254(55),264 Ellfolk, N . , 2 9 3 , 295(13),334, 562(39),577 Elliott , W. B . , 52(278), 54(278).80 El l i s , J . , 118(32). 119(32), 123(32), 127(32),

206(32), 231, 254(53), 256(53), 262(53), 264

Ellsworth, R. K . , 503(30, 31), 527(3 I), 550, 569(103), 579

Elsevier, J. O. , 422(81),477 Elson, C. M . , 350(20), 361(32),364 Elvidge, J. A . , 370( 13), 376(13), 380(55, 56),

381(55, 56), 382(55, 59, 60), 387, 388 Enderman, F . , 366(1),387 Engasser ,G. , 573(132).579 Engelhardt, H . . 556( 14), 565( 14), 577 England, M. T . , 321( 135).338, 501(58),

535(58), 541(58),551 English, E. C . , 58(359), 60(359),82 Eplattenier, F. L . , 409(51), 476 Epstein, L. M . , 450 (198), 451( 198),

454( 198), 459(246), 461(246), 468(198), 480,482

Erdman, J. G . . 299(37).335, 410(63),

423(63), 432(63), 435(63), 440( 173), 447( 173), 449( 173), 459(173),476, 479, 488(10), 490(10),550

Eriksen, L . , 322( 141), 559(24), 560(24), 563(53), 577

Eschenmoser, A . , 16(20), 21(26),26, 427( 103a), 477

Estabrook, R. W . , 41, 42, 43(244, 245), 45, 50(244, 245), 76, 78, 79

Estep, P. A . , 535(47),551 Evans, D. A . , 111(23), 125(23),231 Evans, D. F . , 460(249),282 Evans, N . , 280(32a),287, 574(137, 142),

575(137), 576(142), 580 Evstigneeva, R. P. , 169(85),233, 240(17),

244(29), 250(44, 45), 251(45), 252, 256(44, 45, 48, 49), 258(17), 259(44,45, 49), 262(29), 263, 264

F

Fajer, J . , 9( 13),26, 43, 51(259-261), 79, 462(257, 258),482

Falk, H.,427(103a),477 Falk. J. E . , 41, 42. 44(143), 76, 77, 290(la),

291( la), 292( l a , 9), 295(la), 297(la), 298, 299( la), 300( la), 304(50), 308(la), 309( la), 310( l a , 50), 31 l ( l a , 50, 76), 318(1 a), 3 19( 1 a), 320( 1 a), 334, 335, 336, 390(1), 392,409(1),417, 429(1), 453(1), 459( 1), 460(. 1),474, 488( 12), 490(12), 491( 12), 505(12), 550, 554(1, 2), 560(1), 565(71),576, 578

Faroog, S., 21(26),26 Fase l la ,P . , 573(132),579 Felton, R. H . , 9(13),26, 43, 51(259-261), 79,

423(86), 450(86), 454(86), 462(256-258), 463(256), 473(287),477,482, 483, 571(115), 572(115), 573(115),579

Ferguson, J. A . , 437( 132), 439( 132), 447( 164), 448( 164), 464( 164), 465(164), 478, 479

Ferramola, A . M . , 280(32a), 2S7 Fersht, A. R. , 47( 166), 48(166), 66(166),

67(166), 68(166), 76 F e u t r i l L G . I., 254(55),264 Ficken, G. E . . 370( 15), 371(17), 372(15, 21),

378(15),J#7

Finarelli , J. D . , 92(38), 94(38), 98(38), 100, 572(124, 125), 579

Finarelli , M. G . , 89(34), 92(38), 94(38), 98(38), 100

Fink, E , 104, 105,2 ?/ Finkeman, R. B . , 535(47),551 Fischer, H . , 3, 4(4-6), 5(5), 6(5), 8, 14( 19),

105,26, 32, 33(54, 66, 67, 69, 70, 73, 74), 38, 39, 40(54), 43, 44, 50, 51(54, 246, 250), 54. 55(58, 73, 304, 313, 314), 56, 73, 79, 80, 85,87,99, 104, 107(14), 145(14), 146(14), 147(67), 151, 168(14), 177(14), I82( 14), 206(93), 209, 210,2.?/, 233, 234, 235(2, 3), 244(28), 249(43), 256( 1),26J, 264, 265(1), 266(9), 269(9, 2 l -22b, 23a), 277(31), 281(32e), 282, 283(42),286, 287, 288, 290(3), 291, 293(15), 294(19, 20), 295(23), 297(26), 299(20, 23), 300(19), 302(43a), 305(51), 317( 111), 318(111), 319, 324(147, 148), 327(156, 157, 159, 163), 328(166), 329(167). 331( 177), 332, 333(175, Mb),334, 335, 337,338,339, 336(1, 2), 369(9, 10, 11), 387, 392(3, 4), 393(3, 4), 406(41), 408(41), 409(3, 4, 53), 410(3), 414(3, 4), 425(41), 426(41), 447(3, 4), 449(3, 4), 450(3,4, 188), 453(3, 188), 454(3, 188), 459(3), 460(3),474, 476, 480

Fisher. R. G . , 443( 150),479 Fitssimmons, B. W . , 450(208), 454(208),4#/ Fitzgerald, A . , 432( 128a), 434( 128a),478 Flaugh, M. E . , 252(52), 264 Fleischer, E. B . , 50(219), 78, 354(25).

363(36), 400(31), 424(137, 138), 440(137, 138), 441(137), 442( 142), 444(142), 446(137. 138), 447(166, 180, 186), 448(166), 449(166, 180, 186), 451(210), 454(210), 468(277), 469(277), 471(277, 281). 473(186),475, 479, 480, 481, 483, 569(100), 579

Fletcher. S. R. , 444(155),479 Fliniaux, B . . 398(24a), 422(24a), 423(24a),

432(24a), 433(24a), 436(24a), 438(24a), 440( 24a), 475

F l o n a n . C 409(51),476 Florian. R. , 471(281). Folz, M . , 404(40), 407(40), 419(22), 422(22),

423(40), 431(40). 432(40). 433(40), 436(40), 438(40),475, 476

Foner .S. , 451(218), 454(218). 460(2 18),481 Fontesse. M.,422(23a),423(23a),432(23a),

433(23a),435(23a, 130a), 436(23a), 438(23a),440(23a), 475

Fookes, C. J. R. , 146(65), 147(68a), 185(66), 232, 233, 249(42), 253, 255(42), 256(42), 259(42), 264

Forman, A . , 51(260), 79, 262(258),482 Foukes, C. J. R. , 307(56), 312,336 Fournari, P . , 398(24a), 422(23a, 24a),

423(23a, 24a), 432(23a, 24a), 433(23a, 24b), 435(23a, 130a), 436(23a, 24a), 438(23a, 24a), 440(23a, 24a), 475

Fox, H. M . , 41, 45(150), 55(150), 76 France, H.,370( 14),387 Francesconi, L . , 573(132),579 Francis, J. N . , 447( 162), 448( 162), 449( 162),

465(162), 466(162),479 Frank, B . , 319(121),337 Frankel, R. B . , 451(218, 224), 454(218, 224),

460(218, 424), 43/ French, J. M . , 9(9), 26, 244(27),263,

321(132, 135, 138), 322(139, 140),338, 501(58), 535(58), 541(58),551

Freund, E . ,385 ,JSS Friedrich, W . , 366(2) 387 Frisse, M. E . , 450(206), 454(206), 465(206),

466(206), Fronek, A . , 58(355), 60,52 F r y d m a n , B . , 125(41), 126, 135(55), 232,

316(108),JJ7 F rydman ,R . B . , 316( 108),337 Frye. D. A . , 177(45),388 Frye, J. S.. 462(253),482 Fuchsman,W. H . , 3 15( 103),337, 440(172).

447(172), 449(172), 450(172), 45K 194), 453( 194), 454( 172, 194), 458( 172), 459( 172. 243), 460( 172), 461( 194), 479,480, 568(96), 578

Fuhrhop, J . -FF, 88( 13), 99, 294(21),335, 406(43, 45), 409(43), 410(55, 56), 415( 122). 425(43, 45, 105), 426(43, 45). 427(45, 55), 429(43), 432(45, 122), 433(45), 435( 122). 447( 184, 185), 449( 184, 185), 453(43), 463(56), 472( 185), 473(55, 185),476, 478, 480, 502(27),550, 558(19),577

Fujimoto, W. Y. 291(6), 292(6, 10), 294(6), 295(6), 296(6), 298(6), 299(6). 300(6), 301 (6), 302(6), 303(6),334, 568(93),578

Fujita, I.. 473(287),483 Funke, O . . 55(306) Furhop, J . , 302(44), 333(44),335

G

Gagne, R. R . , 89(32) 100, 450( 199), 453( 199), 454(199) ,455(199), 456(199), 465(199), 466(199), 468(267), 469(267), 482

Gajdos, A , 3 7 , 42, 46(99, 100), 74 Gajdos-Torok, M . , 37, 42, 46(99, 100), 74

562(35), 566(35),577 Gallagher, W. A . , 52(278), 55(278),#0 Gallegos, E. J . , 521(42),557 Games, D. E . , 278(44), 280(32a), 283(43, 44),

284(43), 285(43), 287, 288, 322( 142), 327(142),338, 378(50), 379(50),388

Gantz, D . , 319(121),337 Garofalo, J . , Jr.,472(284),483 Gast, J. H . , 565(70), 578 Gaudenz i ,T . F . , 34(77), 73 Gebala, A. E . , 354(26a), J64 Gehring-Miil ler , R . , 30(21), 40(136), 67(21),

72, 75 Geibel , J . , 450(203), 454(203, 226), 455(203),

458(226), George, P . , 42, 46, 48(158, 159), 49(186),

67(158), 76, 77, 95(42), 100 Gerald, P. S., 67, 69(381),82 Gewitz , H. S., 311(79), 313(86, 88, 97), JJ6,

337 Giannini , D. D . , 108(19),231 Gibbs, E . , 573(132),579 Gibson, J F , 42( 173), 77 Gibson, K. H . , 111(23). 125(23),231 Gibson, Q H , 42( 172), 48( 172), 77 Gieren, A . , 398(26), 399(26), 436(26),475 Gilchrist , M . , 54(297), 55(297),Stf Gilder, H , 39, 40(108), 74 Gillette, J . , 43(245), 50(245), 79 Glebovskaia, E. A . , 486(3), 507(3), 539(3),

550 Gle im, W . , 3 3 , 7 J , 85,99 Goddard, D. R . , 30, 42, 71 G o e b e K S . , 409(53), 476 Gogan, N. J440(145),479 Goldberg, A . , 32(50), 39, 40(50), 73 Goldberg, D. E . , 351(24a),J64 Golden, J. H . , 380(56), 381(56), 382(60), J&S Goldmacher, J . , 89(34), 100 572(124),579 Gonzalez, B . , 442( 141), 443( 141),479 Goodman, M . M . , 563(55),578 Gore, P. H . , 267(16),286 Gottwald, L. K . , 89(31), 100

G 6 t z , H , 33(63), 73 Gouterman, M . , 43(218), 50(218), 51(249,

258), 78, 79, 306(55),336, 378(51,52), 338, 407(46), 415(66), 417(66, 72), 423(65), 427(65), 429(46), 430(46), 431(46, 115), 432(46, 125, 128b), 433(125),436(46),437(125, 128b), 440( 136), 441( 136), 465(260), 466(260), 468(276), 469(276), 471(276),476, 478, 479,482,483, 544(61),557, 571(113, 114), 572( 129a), 579

Grabar, P. , 58(356), 60,82 Grabe, H . , 49,77 Gradyushko, A . T . , 89,700 Granick, S., 36, 37, 39, 40(90, 108), 41, 42,

44(269, 270), 46(89, 100), 48(87-90), 51(269, 270), 64, 65, 69(375-378), 74, 79, 82, 309(67), 320(131), 323,336, 338, 409(52), 426(52),476, 561(28), 565(69), 577, 578

Grassl , M . , 311(77, 83),336 G r a y , C . H . , 32(53), 73, 318(112), 320(129),

337, 338, 574(138, 139, 140, 142), 576(138, 139, 140, 142), 580

Grayson, D. H . , 322(143),338 Green, A . A . , 565(67),578 Green, J. G . , 498(23), 550 Greenlee, W . F . , 108(19),231 Gressl , M . , 43(223), 50(223), 78 Griffith, J. S., 456(228),281 Grigg, R . , 21(27, 28),26, 155(78), 159(78),

208(105), 224(114), 225(1 \4),233, 234, 240( 14), 241 (19), 242(21), 243(25), 244(21, 25, 26), 246(14, 19, 21, 36, 38), 248(40), 256(19), 258(14, 21), 261(14, 21), 262(25, 26),263, 264, 304(53), 305(53), 321(53, 136),335, 338, 342(4), 345(12), 346(414, 14b, 16), 347(4, 18), 351(4), 353(4), 354(4), 357(16, 29), 358( 14, 29, 31), 359(29), 360(16), 361(29),363, 364, 366, 367(7), 368,557, 447( 179), 449( 179), 468( 179, 272), 469(179, 272), 470(179, 212),480, 483, 544(63), 551

Grimes, C. J . , 440( 139), 441 (139),479 Gr ins t e in ,M ,291 , J J4 Grossman, J . , 573(130),579 Guilard, R . , 398(24a), 422(23a, 24a),

423(23a, 24a), 432(23a, 24a), 435(23a, 130a, 131a), 436(23a, 24a, 131b),

438(23a, 24a), 440(23a, 24a),475, 478 Guiodotti , W . , 30(20), 67(20), 72 Gunsalus, I . C , 417(72),476 Giinther, H . , 32, 61(364), 72, 82 Gupta, P . C , 224(111), 225(111),234,

278(32c),280(32c), 287 Gurinovitch, G. P . , 367(8), 369(8),387 Gurinovitch, I. E . , 367(8), 369(8),387 Guryshev, V . N . , 252(48), 256(48),264 Gutman, H. R . , 31(31), 61(31), 72

H

Haagen-Smit, A. J . , 42( 174), 48(174), 77 Haas, 55(311), 56(311),50 Haber l and ,H . , 367(9),387 Haberland, H. W . , 14(19), 15,26 Haberle, N . , 43(262), 79, 88, 95(11), 96, 97,

98,99 Habets, H . , 404(40), 407(40), 423(40),

430(40), 433(40), 436(34), 438(34, 40), 476

H a g e r . L . , 563(46), 577 Hagihara, B . , 55(320, 321, 322), 56(320-

322), 81 Hahn, P. F . , 62(368), 69(368),82 Hai, T. T . , 224( 111), 225(11 \),234, 278(32c),

280(32c), 287 Halbert, T. R . , 89(32), 100, 450(199),

453(199), 454( 191, 199), 455( 199), 456(199), 457(232a), 465( 199), 466(199), 480,481

Halbig, P. , 206(93),233 Hale, J. H . , 311(76), 313(91),336 Halpern, B . , 44(275), 51(275), 52(275), 79, 80 Hambright, P . , 356(26c), 363(33),364,

392(10, 11),393(10, 11),410(10, 11), 423(11, 90, 93), 424(93), 451(215), 454(215), 459(93), 461(93), 462(215), 475,477,481

Hamilton, A . , 264(39),264, 350(20),364 Hamilton, R. J . , 345(12),363, 367(7), 368(7),

387 Hamor, M. J . , 50(221). 67(221), 78 Hamor, T. A . , 50(221), 67(221), 78 Hanania, G. 1. H . , 42( 158), 46(158), 48(158),

67(158), 76

Hanauer ,R . , 88(14),99, 115(30b), 117(31), 123(31), 127,231, 410(61), 421(61), 427(61), 447(61), 449(61),476

Hanbright, P . , 342(5), 343(5),363 Hannah, J . , 8(7b),26, 236(6), 238(6).263,

281(34), 287 Hanson, J . C, 468(276), 469(276), 471(276),

483, 571(114),579 Hanson, L. K . , 407(46), 417(72), 421(46),

423(46), 424(136), 429(46), 430(46), 431(46), 432(46), 434(46), 436(46), 440( 136), 441 (136), 468(276), 469(276), 471(276),476, 478, 483, 571(114),579

Hanson, W. E . , 410(63), 423(63), 432(63),

435(63), 476 Hanstein, A . , 58(360), 60(360),82 Hantzsch, A . , 129(49),232 Hardegger ,B. , 21(26),26 Harding, M . J . C , 407(47), 425(47),476 Harkness, A . L . , 25(31),27 Harley, J . , 61(363),82 Harowitz, F . , 41, 45( 147a), 76 Harris , J . L . , 562(33),577 Harris , R. L. N . , 94(40), 100, 151(72, 73),

153(75), 154(75), 155(75), 156(72,79), 193(96), 202(72), 207(72, 73), 233, 240(15), 241(18), 242(21, 23), 243(23), 244(21), 246(21, 37), 249( 15, 22), 256(15), 258(21), 259( 15), 261(21, 22, 23), 262(23), 263, 327(162), 329( 162, 168), 339, 366(3), 387, 568(92), 578

Hartree, E. F . , 30, 36(5), 42, 71, 78 Hauck, F. P . , 8(7b),26, 236(3), 238(6),263,

281(34), 287 Haurowitz, F . , 58(345), 59,81, 440(177),

447( 177), 449( 177) ,473(177), 480 Hausser. K. W . , 49, 77 H a w k e s , G . E.,431(113),478 Hayes, A . , 115(30), 125(30), 126(30),

127(30), 145(30), 174(88), 231, 233, 265(2), 286

Hayes, R. G . , 423(97),477 Hazeldine, D. J . , 378(49),388 Heckmaier, J . , 327(156),338 Heftman, E . , 554(8),576 Heidner, E. L . , 47( 167), 66( 167), 67(167), 76 Helberger, H . , 235(3),263 Helberger, J. H . , 384(61, 62, 63),388 Henderson, L. J . , 39, 40(125), 75 Henderson, R. W . , 566(78),578

Hendry, J. L . , 3 1(34), 72 H e n z i , R . , 409(51),476 Hermanek ,S . 556(11),576 Hernandez, R. , 556(12),576 Hernandez, R., Jr., 556(12),576 Herout, V . , 542(59), 551 Hess, K . , 108(20),231 Hess, P. , 105(11),231 H e v e r , D . B . , 384(63),388 Hilger, J . , 33(67), 75, 319(125),JJS H i l l , H . A . O . , 451(214, 220, 222), 454(214,

220, 222), 457(238), 461(214. 250),481, 482

H i l l , H . C . , 378(49),378 H i l l , R. J . , 30, 30(20), 67, 71, 72 , 309(61),

336, 424( 101), 429( 1), 437( 101), 477 Hilschmann, N . , 30(21), 40( 109d), 67(21),

72, 74 Hilse, K . , 30(21), 40(109d), 67(21), 72, 74 Hintermeier, K . , 107(15), 108(15), 112(15),

124,231 H i r a y a m a , N . , 363(35),364 Hisey, A . , 53, 54, 55(295),tf0 H o . C, 47(165, 167), 66(165, 167), 67(165,

167), 76 Hoard, J. L . , 43(218), 43(222), 50(221, 222),

51(222), 67(221), 78, 393( 16), 397( 16, 25), 398(25), 422(25), 423( 16, 25), 425(106), 426(106), 432(16, 25), 433(25), 436(16, 25), 437(16), 438(16, 25), 440(25), 450( 195), 454( 195), 456( 16, 229), 457(229), 468(264), 469(264),475, 478,480,482

H o b o m , G . , 30(21), 67(21), 72 Hodgkin, D . C , 357(30),364 Hodgson, G. L . , 121(33), 135(59), 141(59),

155(77), 163(59,77), 169(59), 172(59), 232, 233, 244(33), 248(33), 260(33), 262(33), 264

Hodgson, G. W . , 44, 51(274, 275), 52(274, 275, 277), 79, 80, 501(32), 503(32), 517(39), 520(32), 522(32), 550, 551

Hodson, G. L . , 574( 140), 516(140),580 Hofelmann, H . , 146(67), 147(67),233 Hoffman, B. M . , 443(149, 150). 451(219),

454(219), 457(237), 460(219), 468(237, 262),479, 481,482

Hoffman, L. M . , 447(161, 162, 163),

448(161, 162, 163), 449(162), 464(163), 465(161, 162, 163), 466(161),479

Hogeboom,G H 3 0 , 71 Hogness ,T. R . , 44(267), 51(267), 79 H o l d e n , H F , 3 0 , 7 / H o l m , R H , 444( 156), 447(167, 168),

448(167, 168), 451(218, 224), 454(218, 224), 460(218,424), 465( 167), 466( 167), 479,481

Holt, A. S., 25(30),27 H o l t , L B , 320(129),338 Hood, A.,498(22),550 Hopf, F. R . , 400(30), 423(92), 447(30, 92,

160, 164), 448(30, 92, 160, 164), 449(30. 160), 452(92), 464(92, 164), 465( 160), 466(160),475,477,479

Hoppe, W . , 398(26), 399(26), 436(26),475 Hoppe-Seyler, F . , 9 , 2 6 , 35(80, 81), 52, 54,

73,80 Horchner, P. , 574(143),580 H o r i o , T . , 55(322), 56(322),81 Horrocks, W. Dew. , Jr., 421(116, 117),

422(116),429(116, 117), 430(116, 117), 431(116, 117. 120),432(116, 117, 120), 433(116), 436(116),478

Hotchk i s s ,R D , 3 0 , 7 / Houghton, L. E . , 267(12a), 268(12a),

269(12a), 271(12a), 286 H o w a r t h , T . T . , 104(9), 153(76), 218(9),231,

275(45a), 278(45a), 283(45,45a), 284(45, 45b),288, 328(165), 329(165),339

Howel l , D. B . , 572(129a),579 Hrung, C. P. , 399(27), 408(27), 425(27),

440(27), 442(27), 446(27), 447(27),475, 569(102), 579

Huang, W. Y. 513(35), 514(36), 515(36),551 Huber, P. R . , 573(132),579 Hudson, M. F . , 147(68b), 156(68b),2J3,

402(36),420(108), 425(108), 426( 108), 427(36, 108), 431( 113),475, 477,478, 572(128), 579

Huennekens, F. M . , 89(22, 23), 100, 416(68), 424(68), 425(68), 447(68), 449(68), 453(68), 476

Huff, J . , 450(200, 201), 454(200, 201), 455(200, 2Q\),480

H i i f n e r , G . , 53, 55(290),80 H u g g i n s , W , 5 7 , S /

Hui, E.,472(131),47S Hiinefeld, F L , 38, 40( 113), 55( 113), 75 Hunt, E . , 111(24), 124(24), 125(24), 135(59),

141(59), 153(24), 154(24), 160(24), '163(59), 169(59), 172(24,59), 180(24), 224(24), 225(24),231,232

Huper, F . , 319(121),337 Huppatz, J. L . , 193(96),233, 241(18),

246(37),263, 264 Hunap, B. S., 315( 105),337 Husain, S M , 450( 189) 453( 189), 454( 189),

480 Hush, N . S . , 377(46),388 Huttquist, D. F . , 576( 144),580

Iber. P. K . , 342(3), 346(3), 347(3),363 Ibeis. J. A . , 89,100, 447(167, 169), 448( 167,

169), 450(204a), 451(217, 218,224), 454(204a, 217, 218, 224), 460(218, 224), 465( 167, 204a), 466( 167, 204a), 468(261, 2b9),469(269),479, 481,482

Ichakawa, M . , 409(50), 440(50), 441( 135), 476,478, 569(101),579

Ihara, M . , 121(33), 155(77), 163(77),231, 232, 233, 244(33), 248(33), 260(33), 262(33),264, 320( 126), 338

Ikeda, K . , 309(69),336 Imbler, P . , 572( 122),579 Ingalls. E. N . , 49(184), 77 Ingram, D . J . E . , 42( 173), 48( 173, 179), 67,

77 Ingram, V. M . . 30(24), 39,40(24), 42( 179),

69(384), 72, 77 Inhoffen, H. H . , 44(252, 253), 51(252, 253),

79, 88(13), 99, 293(17, 18), 302(44, 45), 304(17, 18), 305(18), 306( 18), 307, 333(44),335, 392(9), 409(9), 410(59), 427(73), 429( 118), 447(59, 184), 449(59, 184), 473( 18), 474(73),475, 476, 477, 478,480 , 502(27),550, 568(94),578

Inman, J. K . , 64(2, 72), 69(372),82 Isenring, H. P . , 427(103a),477 Itano, M. A . , 30, 58(352), 60, 72

Ito, S.,8(7b),26, 236(6), 238(6), 263, 281(34), 287

J

Jackson, A. H . , 104(9), 115(30a), 116(30a), 118(32), 119(32), 121(34), 123(32), 126(43), 127(32), 134(53), 146(44), 148(69), 153(76), 162(82), 165(69), 177(89), 195(44, 99), 206(32), 216( 107), 217( 108), 218(9, 69), 220(69, 89), 224(89, 112), 225(89, 113), 226(89),231, 232, 233, 234, 237( 11), 244(30, 3',), 252(50), 254(53), 255(56, 59), 256(53), 257(30, 34), 56, 60, 61), 260(34, 56, 60, 61, 62), 262(53),263, 264, 265(4), 266(7), 267( 12-12b), 268( 12-12b), 269(7, 12-12b), 271(7, 12-12b), 273(26), 274(4. 29), 275(7, 26, 32, 38, 39, 45a), 276(30), 278(29,32,38,39,40,41a,44,45a.45b, 47), 279(32), 280(32a, 32b). 281(29, 37, 38. 39, 40, 41a), 282(38, 39), 283(39, 43-45b), 284(38, 43-45b, 47, 48. 51, 52), 285(43), 286, 287, 288, 292(12), 304. 320( 127), 321( 137), 322(142), 323( 144), 327(142), 328( 165), 329( 165),334, 335, 338, 341(2), 345(2, 13), 346(15), 347( 18), 348(2), 351(2), 354(26), 355(26), 360(26), 363, 364, 367(6), 378(50), 379(50),387, 388,54[(51),551, 566(79), 570(79), 574(137, 142), 575(137), 576(142),578, 580

Jackson, J. R. , 283(43), 284(43),288 Jacob, F.,37(97a),74 Jiiger, P . , 392(9), 409(9),475 J a h n , F . , 54, 55(298),30 Jain, A. C, 1 18(32), 119(32), 123(32),

127(32), 206(32), 231, 254(53), 256(53), 262(53), 264

James, B. R . , 468(261,273, 274), 469(273, 274), 470(273, 274), 482,483

James, K. J . , 322(\43),338 Jandl, J . H . , 64, 69(372),82 Jandorf, B . J . ,31(31), 72 Janson,T. R. , 25(31),27, 400(32), 401(32),

402(32), 475 Jaquet, A . , 52, 53, 55(282),80

Jayne, D . , 450(21 la), 454(21 la),481 Jensen, J . , 562(41), 563(41),577 Jensen, L. H . , 432( 128a), 434( 128a),478 Johnson, A. W . , 21(28),26, 43(264), 51(264),

79, 94(40), 100, 104(7), 117(7), 122(5, 7), 123(5,7), 126(5,7), 127(5), 145(7), 151, 155(78), 156(72), 159(78), 169(78), 187(95), 193(96), 202(72), 205(95), 206(84). 207(72, 73), 208(105), 224( 114), 225(114), 231, 233, 234, 237(7), 238, 240( 14), 241( 18, 19), 242(21, 23), 243(23, 25), 244(21, 25, 26), 246( 14, 19, 21, 35, 36, 37, 38, 39), 248(40, 41), 249(22), 250(46), 254(55), 256(7, 19), 258(7, 14, 21), 259(7), 260(41), 261(14, 21, 22, 23), 262(23, 26), 269(20, 22), 26?, 264, 304(53), 305(53), 321(53, 136), 327( 162), 329(162, 168), J J5 , 338,339, 342(4), 346(4, 16), 347(4, 18), 350(20), 351(4, 21), 353(4), 354(4, 26), 355(26), 357(16, 28, 29), 358(29, 31), 359(29), 360(16, 26), 361(29, 32),363, 364, 366,387, 440(176), 447(176, 179), 449(176, 179), 468( 176, 179, 272), 469( 176, 179, 272), 470(179, 272), 472( 179), 480, 483, 544(63), 551, 570(110), 579

Johnson, F. M . , 51(276), 52(276),<W Johnson, J. F . , 400(33), 408(33), 423(33),

424(33), 432(33), 434(33), 436(33), 444(33), 463(33), 475

Johnson, L . , 566(76), 568(76), 578 Jolles, A , 36, 74 Jones, D. M . , 224( 113), 225( 1\3),234 Jones, J. G . , 450( 189), 453( 189), 454( 189),

480 Jones, O . T . G . , 297(25),335 Jones, P. , 454(21 lb),481 Jones, R. A . , 89, 90, 91(27), 94(27), 97(27),

100, 153(75), 154(75), 155(75), 156(79), 233, 240( 15), 249( 15), 256(15), 259( 15), 263, 568(92), 572( 118), 578, 579

Jones, R. T. , 70(394),83 Jones, R. V. H . , 242(24), 257(24), 262(24),

263 Jope, H . M . , 54(297), 55(297),80 Jordan, E . , 332,339 j0rgensen,S. K . , 32(51), 73 Jorpes, J. E . , 38(105), 74 Jozefawicz, M. L . , 345(\2),363, 367(7),

368(7), 387 Judge, J . , 153(76),233

K

Kadish , K . , 447( 185), 449(185), 462(255), 472(185), 4 7 3 ( 1 8 5 ) , ^ , 482

Kaduk, J . A . , 470(280), Kajiwara, S., 43(233), 50(233), 55(233), 56,

78, 135(56), 232 Kalenda, N. W . , 410(63), 423(63), 432(63),

435(63), 476 Kalmus, E . , 58(340), 59 ,5 / Kamen, M. D . , 44, 51(271), 79, 309,

315 (104 ) ,m J J 7 Kammerer, H . , 33, 73 Kammerling, S. E . , 42(211), 78 Kampas, F . , 51(256), 79, 408(49), 424(49),

440(49), 441 (49), 476, 572( 129), 579 Karayannis, N. M . , 488( 18), 489( 18),

491(18),550, 569(107, 108),579 Kane, A. R . , 400(32), 401(32), 402(32),475 Kassner, R. J . , 450(202), 454(202), 455(202),

458(202), 450 Ka tz , J. J . , 19(24), 25(31, 32),26, 27,

395(20), 423(20, 88), 426(103), 427(103), 439(88),475, 477, 568(98),579

K a y , I. M . , 30(18), 72 K a y , I. T . , 94(40), 100, 151(72, 73), 156(72),

169(84), 193(96), 202(72), 206(84), 207(72, 73), 233, 237(7), 238, 240(13), 241(18), 242(21, 23), 243(23), 244(21), 246(21, 37), 249(22), 256(7), 258(7, 21), 259(7), 260(41), 261(21, 22, 23), 262(23), 263,264, 269(20),287, 327(162), 32%(\62), 339, 357(28),364, 366(4),387, 440( 176), 449( 176), 468( 176), 469( 176), 480

K e h l , R . , 559(23), 560(23),577 Keighly, C . , 42(174), 48(174), 77 K e i l i n , J , 358(36), 60,52 Ke i l i n , D , 30, 36(5), 40(132), 42(156),

46( 156), 48( 156), 57, 58(156, 326), 59, 67(156),7/, 75 , 76, 78,81, 309(61),336

K e l l y , A H , 135(58),232 Kendrew, J. C, 30, 39, 40( 109a), 41(140),

42( 161), 44, 45(10), 48(161), 67(161), 69(380), 71, 74 , 75 , 76

Kennedy, G. Y . , 278(40), 281(40),288, 323(144), 338

Kennedy, R. R . , 53, 54, 55(294),80 K e n n e r , G . W . , 104(9), 107(13), 111(30,

30a), 116(30a), 1 18(32), 119(32, 32a), 121(34), 123(32), 125, 126(30,44),

127(30, 32,44a), 134(53), 145(30), 146(44), 148(69), 153(76), 161(81), 162(82), 165(69), 170, 174, 177(89), 179, 195(44, 99), 206(32), 216(107), 217( 108), 218(9, 69), 220(69, 89), 224(89), 225(89), 226(89), 231, 232, 233, 234, 237( 11). 242, 244(34), 252(50), 254(53). 255, 256(53), 257(24, 30, 34, 56, 60, 61, 62), 260(34, 56, 60, 61, 62), 262(24, 53), 263, 264, 265(2, 4, 6), 266(7), 267(12), 268( 12), 269(7, 12), 271(7, 12), 273(26), 274(4, 29), 275(7, 26, 32, 38, 39,45a), 276(30), 277(31a), 278(29, 31a, 32, 38, 39, 40, 41a, 45a, 45b, 54, 55), 279(32). 281(6, 29, 3 l a , 37, 38, 38a, 40, 41, 41a), 282(38, 39), 283(39, 45-45b), 284(39, 45-46, 51, 52), 285(53-55), 286, 287, 288, 292(12), 302(48), 304(52), 320(127), 321(137), 323(144), 328(165), 329, 332( 173), 334, 335, 338, 339, 345(13),363, 541(57),55/, 566(79), 570(79),578

Kenney, M. E . , 379(53), 380(53),388,

400(32), 401(32), 402(32, 38), 432( 124), 433(124), 437(124, 133), 473(38),475, 476,478

Kenny, J. E . , 426(77), 452(77), 465(77), 466(77), 467(77),477

Kenyon, R. W . , 208(105),234, 240(14), 243(25), 244(25), 246( 14), 258( 14), 261( 14),263, 304(53), 305(53), 321(53), 335

Kephar t , J .C. ,325(152) ,JJS K h a l i L G E , 407(46), 421(46), 423(46),

424( 136), 429(46), 430(46), 431(46), 432(46), 433(46), 436(46), 440( 136), 441(136),476, 479

Kiese, M . , 313(89, 90, 95),336, 337, 564(61), 578

K i m , J. B . , 51(256), 79, 89, 92, 96, 98,100, 408(49), 424(49), 440(49), 441(49), 476, 572(125, 129), 579

K i m , N . , 397(25), 398(25), 422(25), 423(25), 432(25), 433(25), 436(25), 438(25), 440(25), 450( 195), 454(195), 475, 480

K i m , Y C , 125(42), 147(42),232 Kincaid , J.,451(213), 454(213), 459(213),

461(213), King , E J , 54, 55(297),SO K i n g , T E , 43, 50(230), 78 King, T J , 346(14b),363 King, T. L . , 346(14), 358( 14),363

Kirk land , J J 558(17),577 Kirner , J. F . , 442(141), 443( 141), 472(284),

479, 483 Kirshner, W. B . , 88(15), 99 Klarer , J . , 33(71), 73 Kleinspehn, G. G . , 104, 105,231 Klesper. E . , 494(6), 509(6), 518(6), 520(6),

542(6), 550 K l u m p p , T . G . , 54, 55(299),80 Knight, B . C , 292(9),334 Knorr , L . , 102, 108(20), 129,23/ K n o x , K . , 400(32), 401(32), 402(32, 38),

474(38),475, 476 Kobayashi , H . , 378(51),388 Kobert , R . , 43(234), 50(235), 78 K o c h , S., 451(218, 224), 454(218, 224),

460(218, 224),4#/ Koenig, D F , 50(220), 78 K o g l , F , 331(177), 333(177), J J9 Kok i sch , W . , 422(84), 423(84), 447(84),

452(84), 458(84), 464(84), 465(84), 466(84), 467(84), 468(84), 477

K o l m , H . G . , 124(39), 167(83),232, 233 K o n , H . , 51(265), 79 K o n d o , T . , 284(51),288 Koningsberg, W . , 30, 67, 72 Korber , E , 38, 40( 115), 58( 1 15), 75 Kornis , G . , 134(53),232 Korsakoff, L . , 89(34), 100, 572(124),579 Kosse l , A , 52(280),SO Kouba , J . , 442( 141), 443( 141), 468(267).

469(267),479, 482 Koyano,T ,435(130),441(135),47S,

569(101),579 K o z h i c h , D T ,89 ,100 K r a u s , G , 38, 40(117), 75 K r o l , S , 86, 89(4), 96(4), 99 Krzyzanowska , M , 556( 16), 577 K u b y , S A , 55(319), 56,81 K u h n , R . , 49, 64. 69(379), 77, 82, 134(54),

232 Kulkarn i , B D , 206(103), 234 Kunke l , H . G . , 30,42(23, 177),45(23),

46(23), 48(176, 177), 72 , 77 K u r z , H . , 313(89, 90), 336, 564(61), 578 Kurzinger, A . , 249(43),264 Kiister , W . , 33(72), 73, 503(29), 522(29),550 Kvenvolden, K. A . , 44(275), 51(275),

52(275), 79, 80, 521(41), 55/ K w i r a m , A. L . , 43(258), 51(258), 79

L

Labbe, R. F . , 291,334, 562(40),577 Lachman, M . . 299(38),335, 568(90),578 Ladner, J. E . , 47(165, 167), 66(165), 67(165),

47 La Mar , G. N . , 444( 156),261(251), 262(253),

479, 482 Lamson, D. W . , 297(34), 298(33), 313(33),

335, 563(47, 48, 49, 50), 564(50), 567(50), 569(50),577

Lancaster, E. R . , 41, 45(151), 76 Lane, C , 70(396),83 Lang, G . , 89(32), 700, 450(195, 199),

451(195, 199), 454(195, 199), 455( 199), 456( 199), 465( 199), 466( 199), 480

Langemann, A . , 8(7b),26, 236(6), 238(6), 263, 281(34),287

Lantzke, 1. R . , 454(21 lb),487 Larson, E. A . , 39, 40(130), 75, 462(255),482 Lascelles, J . , 37, 42, 46(98), 74 Laslett, R. L . , 89, 90, 91(27), 94(27), 97(27),

/00, 572(118), 579 Lasz lo , A . , 447( 186), 449( 186), 473( 186),480 Latour, J. M.,435(130a, 131a),478 L a u , D . Y . K . , 147(68a),233 Laufberger, V . . 64, 69(378),82 Laurel l , C. B . , 64(371), 69(371),82 Lavellee, D. K . , 354(26a), 356(26b, 26d),

364, 468(277), 471(277),483 Lawrence, R. D . , 3 1(39), 72 L a w r i e , C . W . , 147(68),233 L a y , K. L.,420(77),432( 127),434( 127),

437( 127), 439( 127), 450( 190), 452(77), 453( 190), 454( 190 212), 458( 190), 459( 190), 460( 190, 212), 462( 190), 465(77), 466(77, 190), 467(77),477, 478, 480,481, 570(112), 572(112),579

Lea l , O , 457(235),481 Lecanu, L. R. , 3 1(32), 72 Lecomte, C . , 398(24a), 422(23a, 24a),

423(23a, 24a), 432(23a, 24a), 433(23a, 24a),435(23a),436(23a,24a, 131b), 438(23a, 24a), 440(23a, 24a),475

Lederer, E . , 33(63), 73 Lee , A . , 572(122),579 Lee , R. Y . , 423(90),477 Leenstra, W. R. , 440( 136), 441( 136),479 Legge , J . W . , 14, 25(16),26, 39, 40( 131), 75,

231,263, 460(248),482

LeGoff , E . , 8(7b), 26, 88, 99, 236(6), 238(6), 263, 281(34),287

Leimgruber, W . , 8(7b),26, 236(6), 238(6), 263, 281(34), 287

Lemberg ,R . , 14, 25( 16), 26, 39, 40(131), 41, 42, 43, 44, 50(227-229), 75, 76, 77, 78, 231,263, 298, 299(30), 304(50), 305(54), 310(50), 311(50, 76, 78), 312(85), 313(96, 98,99, 101), 315(105, 106),335, 336, 337, 366,387, 460(248),482

Leng, J . , 187(95), 205(95),233 Leonard, J. J . , 89, 92, 96(28), 98(28), 100 Lever, A. B. P . . 374(28), 377(28), 379(28),387 Levere, R. D . , 40, 41(110), 46(110), 65,74,

323,338 L e v i , E , 104(2),237 L e v y , E. S., 125(41), 126(41),232 Lexa , D . , 462(254, 255),482 Lichtarowitz, A . , 410(58), 427(58), 447(58),

449(58), 476 Lichtenstein, B . , 459(244), 462(244),482 Liebermann, C , 33,73 Liepa , A. J . , 145(62, 64), 146(65, 66),

151(71), 169(86), 170(86), 175(64), 179(65), 182(65), 182(62), 185(66), 186(71), 195(97), 207(104), 215(62), 216(62), 220(71), 221(71), 223(62), 224(104, 116, 117), 228(104, 116, 117), 229(116), 230(116),232, 233, 234,240, 244(31), 251(31, 47), 252(31), 254(54), 256(16, 31), 258(16), 259(16, 54),263, 264(5), 268(17), 268, 269(19), 281(33), 286, 287

L i l i e n t h a K H R , 451(194), 453(194), 454(194), 461(194), 480

L i m , C K , 574(138, 139, 140, 142), 576(138, 139, 140, 142), 580

Linder, F . , 297(26),335 L i n d e r , R . E . , 423(98),477 Lines, J . , 321(135),338 Lines , M. T . , 501(58), 535(58), 541(58),551 Linschi tz , H . , 571(1 15), 572(115), 573(115),

579 Lins tead ,R. P . , 5(7),26, 87, 88, 96(4), 97,

99, 370(12-15), 371(17, 18, 19), 372(15, 21), 373(22), 374(30, 34, 35), 345(34, 38, 39), 376(13, 19, 42, 43, 44), 377(34, 35, 44, 45), 378(15), 380(54, 56), 381(56, 57, 58), 382(59), 384(65, 66), 386(65, 66), 387, 388, 410(58), 427(58), 447(58), 449(58), 476

Liquori , A M , 56( 163), 76 Little, R. G.,89,100, 447(169), 451(217),

454(217), 468(269), 469(269),479,48/, 482

Ljusberg- Wahren, H . , 468(267), 469(267), 482

Loach, P. A . , 89,100 Lockwood, W . , 298(30), 299(30),335 Loeffler ,R. K . , 565(70),578 Loev. B . , 563(54, 55),578 London, I. M . , 32(52), 41, 42( 175), 44,

46(142),48(I75),7i, 76, 77 Long, J . , 246(35),264 Longo. F. R . , 51(256), 79, 87. 89(34), 92,

94(38), 95(6), 96, 97,98(28, 38), 99, 100, 408(49), 424(49), 440(49), 441(49), 476, 569(104), 572(104, 123, 124, 125, 129), 579

Loock, B.,450(203a),454(203a),455(203a), 480

Looney, F. D . , 224(90), 228(90),233 Loosmore, R. M . , 32(49), 73 Lorenzen, B . , 572(122),579 Lowe, A. R . , 374(34, 35), 375(34, 39),

377(34, 35),388 Lowy. P. H . , 42(174), 48(174), 77 Lubs, H. A . , 372(26), 374(26), 387(26),387 Lucas, J . , 568(89),578 Lueken, H . , 451(214), 454(212, 214),

460(212), 461(214), Luisier, L. L . , 427( 103a),477 Lukyanets. E. A . , 383(60a), J&S Lvowski , W.,8(7b),26, 236(6), 238(6),263,

281(34), 287 Lynen, F . , 43(223), 50(223), 78, 311(77, 83).

336 Lyster, R L J , 42( 186), 49( 186), 77

M

McCombie, S. W . , 278(45b), 283(45b), 284(45b,46) ,2«S, 302(48), 329(48), 332(172, 173), 335,339

McCoy, S. ,43, 50(225), 78, 313(100), 315(100, 103)337, 451(217a),454(2l7a) 481

McDonald, E . , 111(23,24). 112(26), 121 (33), 124(24), 125(23), 135(59), 141(59), 153(24), 154(24), 155(77), 160(24). 163(59,77), 169(59), 172(24,59),

180(24), 224(24), 225(24),231, 232, 233, 244(33), 248(33), 260(33), 262(33), 264, 322( 143),338 574( 140), 576( 140),580

M a c D o n a l d , S . F . , 107, 106(16), 111(27), 113(27), 124, 125(24,42), 129(49), 147(42), 169(87), 177, 184, 187, 190, 195, 206, 207, 208, 220(110), 224(87. 91. 94, 115) , 225(87, 91, 94), 227(115), 23/ , 232, 233,234, 236(4), 263, 265(3), 266(11), 267(11), 268, 271(3), 273(27, 28), 283(28), 286, 287, 310(72), 318( 115, 116) , 319( 119 120), 3 20( 126), 336, 33 7

M c E l v a i n , S M , 129(46),232 M c E w e n , W . , 341( 1), 342(1), 346(1),363 M c G i l l i v r a y , G , 148(69), 165(69), 216( 107),

218(69), 220(69),233, 237( 1 \),263, 267(12), 268( 12), 269( 12), 271( 12), 274(29), 278(29), 281(29),286, 287

McLaughl in , G . , 351(24), 358(24),364 M c L e e s , B. D . , 472(283),483, 568(97), 579 M a c M u n n , C A , 30, 32, 36, 71, 72 Macquet, J. P., 401(35),475 M a h , H . D . , 125(42), 147(42),232 M a k i n e n , M W , 51(265), 79 Makino , R. , 300(40-42),335 Manassen, J . , 473(286),455 Mangoni ,L ,312(84) , JJ6 Mansley, G. E . , 43(229), 50(229), 78 Marchlewski , L . , 38, 39, 40(102), 74 Marchon, J. C, 435 (130a, 13 la), 453( 191).

454(190,478, 480 Margoliash, E , 40( 111 a), 43, 44, 50( 111,

I l i a ) , 51(111a), 67, 74 Mariane l l i ,R . S., 442( 144),479 Maricondi , C , 440( 171), 447(171), 449( 171),

450( 198), 451 (198),453(171), 454( 198), 459( 171), 460( 171), 468(111),479, 480

Markham, E . , 104(5,7), 1 17(7), 122(5,7), 123(5,7), 126(5,7), 127(5), 145(7), 169(84), 206(84),231, 233, 250(46), 264, 269(20), 287

Markovac , A . . 187(94), 190(94), 195(94), 206(103), 207(94), 208(94), 224(94), 225(94), 233, 234

Marks , G. S., 236(4), 263, 310(72), 316(109), 336, 33 7 5 54(3), 565(72), 568(72),576, 578

Markwel l , R. E . , 574( 140), 576( 140),580 Martel l , A. E . , 89,100, 416(70), 447( 182,

183), 449(182, 183),476,480 Mart in , R. A . , 450(208), 454(208),481

Masai , N . , 440( 175), 447(175), 449(175),480 Maskasky, J. E . , 309(71), 311(71), 312(71),

315(71), 316(71),336, 379(53), 380(53), 388, 432( 124), 433( 124), 437( 124), 478

Mason , T. L., 69,82 Mast, E . , 410(62), 429(62),476 Math , V. B . , 240(14), 246( 14), 258(14),

26H 14), 263 M a t l i n , S . A . , 280(32a),287, 574( 137, 142),

575(137), 576(142),580 Matsubara, H . , 55(322), 56,81 M a t s u d a , G . , 40(136), 75 Mauzeral l , D . , 36, 39,40(90), 42(90),

44(272), 48(90), 51(272), 74, 79, 266(8), 286, 302, 320(131), 329(47), 335, 338, 406(45), 425(45), 426(45), 427(45), 432(45), 433(45), 476, 560(25), 577

Maxwel 1, J C , 440( 172), 447(172), 449( 172), 450( 172, 204), 454(172, 204), 456(231), 457(204), 458( 172), 459(172), 460(172). 479, 480, 481

Mayer, A . , 278(53), 285(53), 288 Mayer , F . , 39, 40(128), 75 Mayer , H . , 309(64),336 Mayo , B C , 375(40), 388 Mehne, L . F . , 468(278),483 Menott i , A. R . , 89,99, 424( 100), 425( 100),

426(100), 431(100), 432(100), 433(100), 447( 100), 449( 100), 473(100), 477

Meot-Ner , M , 498(23), 550 Merckl ing , N . , 112(25),231 Metzger, W . , 367(1 \),387 Meyer , E. F. Jr. , 399(27), 408(27), 425(27),

440(27), 442(27), 446(27), 447(27).475 Meyer , P. , 32(57), 73 , 377(48),388 Meyer , T. J . , 423(92), 437(132), 439(132),

447(92, 164), 448(92, 164), 452(92), 464(96. 164), 465( 164),477, 478, 479

Meyer-Betz , F , 32, 73 Michaelis , L . , 45, 51(147), 64(377), 69(377),

76,82 Mieg, M , 488(17), 491(17), 550 Mieg , W ,321(133),JJS MichI, K H , 266(10),286 Mikhalenko, S A , 383(60a),3£S Mi l l e r C K , 50(219), 78 Mil le r , J. R . , 416(68), 424(68), 425(68),

427( 110), 447(68), 449(68), 453(68), 472(110), 476, 478

Mil l ikan , J G , 30( 17), 32(15), 45( 17), 72 Mi l ton , C , 535(47),551 Minnart , K . , 43(239), 50(239), 78 Mironov, A. F . , 169(85),233, 240(17),

250(44, 45), 251(45), 252(48, 49), 256(44, 45, 48, 49), 258(17), 259(44, 45, 49),263, 264

Mirsky , A E , 57, 58(323, 324, 344), 59,81 Mispelter, J . , 462(254),482 Mitchel l , J , 488( 13), 490(13), 501( 13),

505(13), 538(13),550 Mitchel l , S W ,70(391),83 Miyauch i , C , 563(44, 45),577 Moitessier, J . , 57, 58(325), 59,81 Momenteau, M . , 450(203a), 454(203a),

455(203a), 262(252, 254, 255),480, 282 Monod , J , 37, 74 Mooney, J. R . , 377(53), 380(53),388,

402(38), 474(38), 476 Moore , S., 42(177, 178), 48(177, 178), 77 M o r a l l e e , K G , 261(250), 282 More l l , D B , 293(14), 299(31, 32), 313(31,

32, W\),334,335,337 Morgan, V. E . , 55(316), 56,81 Morikawa, I., 55(321), 56,81 Morr ison, D. B . . 53, 54, 55(295),80 Morr ison, M . , 42(207), 78, 311,313(92,93,

94),336, 337, 564(63, 64), 578 M o r s i n g h , F . , 224(115), 227(115),234,

273(27),287, 320(130),338 Morton, R. K . , 41, 42(202), 44,76, 77, 78 Morton , T. C . , 566(78),578 Moscowi tz , A . , 423(98),477 Moser, F. H . , 374(27), 379(27),387, 393(14),

475 Moskowi tz , D. W . , 88(15), 99 M o s s , T . H . , 292(10),334, 451(194),

453( 194), 454( 194), 461(194), 480 Moyer , W. W . , 8,26, 326(154, 155),

321(155),338 Miihlbauer, J . , 33(63), 73 Muir , I M H , 32(53), 73 Muirhead, H . , 68(382), 69(382),82 M u l j i a n i , Z , 306(55),336 Muller , A. F . , 369(9, 10),387 Muller , P . M . , 21(26),26 Muller , R. , 294(20), 299(20),335 Miil ler-Eberhard, U , 58(358-360), 60,82 Munck, E . , 423(95), 461(95),477

Mundschenk, H . , 562(37), 564(56, 57),577, 578

Mustacich, R . , 450(211 a), 454(21 la),481

N

Nakamoto, K. , 440(175), 447(175), 449(175), 451(213), 454(213), 459(213), 461(213), ' 480, 481

N a n z y o , N , 309(68),336 Narasimhulu, S., 43(243-245), 50(243-245),

78, 79 Nasralla, S. M . , 244(29, 32),244, 262(29),

263 Neel, J V , 42, 48(180, 181), 77 Negelein, E . , 4 9 , 55(311, 312), 56(311, 312),

77,80, 313(87), 336 Neilands, J. B . , 54(305), 55(305),80, 309,

336 Nemir, P. , Jr., 58(354, 355), 60,82 Neuberger, A . , 32, 73, 343(9), 344(9), 345(9),

363(9), 363 Neumann, W . , 406(41), 408(41), 425(41),

426(41), 476 Newman, D. J , 153(76), 233 Newton, N . , 43(227), 50(227), 78 Ng, G . , 451(215), 454(215), 462(215),481 Nichol , A. W . , 146(65), 147(68a), 151(71),

179(65), 182(65), 186(71), 220(71), 221(71), 224(90, 109), 228(90, 109), 232, 233,234, 267(14), 268(17, 19) 269(19, 23), 286, 287, 302(46), 315(105), 335, 337

Nicholas, R. E. H . , 318(117),337, 556(13), 561(22), 567(13), 576, 577

Nicholson, D . C , 284(51),288, 318(112), 322(139),337, 338, 574(139), 576(139), 580

Nicolaus, R. A . , 312(84),336 N i e m , T . , 473(287), 483 Niemierko, W . , 556(16),577 N i s h i d a , G , 291,334 Nishikawa, S., 561(27),561 Nixon , L . , 111(23), 125(23),231 Noble, E. P. , 380(54),388 Norman, G- D . . 19(24),26 Noro, K . , 501(60), 543(60), 544(60),551 Noro, T. , 501(60), 543(60), 544(60),551 North, A . C , 68(382), 69(382),82 Nozaki , M , 55(321), 56,81

Nutter, J . , 562(40),577 Nygaard, A. P. , 50, 77 Nyho lm, R S , 42(201), 77

O

O'Br ien , J. R. P . , 54(297), 55(297),80 O'Br ien , T. P. , 400(30), 427(30), 447(30),

448(30), 449(30), 475 Oester, M. Y . , 410(61), 421(61), 427(61),

447(61), 449(61),476 Ogawa, S., 278(54), 285(54), 288 Ogoshi, H . , 363(34, 35),364, 399(29),

440(175), 447(175, 178), 449(175, 178), 451(213), 454(213, 223), 457(223), 459(213), 460(247), 261(213), 268(29, 178), 269(29, 178), 260(178),475,480, 481

Ohnishi , T . , 43(234), 50(234), 78 Oinuma, S., 57(324), 58(324), 59,81 Okada, K . , 135(56),232 O'Keefe , D. H . , 292, 309(71), 311(71),

312(71), 315(71), 316(71),334,336, 450(193), 451(193, 194), 453(193, 194), 454(193, 194), 458(193), 461( 194), 466(193), 480

Okunuki , K . , 55(320-322), 56(322),81, 315(104), 337

Oldfield, D . , 43(264), 51(264), 79, 570(110), 579

Olson, L. W . , 444(153), 450(207), 454(207), 458(207), 465(207), 466(207),479, 481

Omura, T . , 346(14a),363, 399(29),475, 447( 178), 449( 178), 468(29, 178), 469(29, 178), 4 7 0 ( 1 7 8 ) , ^

O ' N e a l , M . J . , 498(22),550 Orten, J . M . , 568(89),578 Orth, H . , 3, 4(4, 5), 5(5), 6(5),26, 36(54),

33(54), 38(54), 39, 40(54), 44, 50(54), 51(54), 73, 107(14), 145(14), 146(14), 151(14), 168(14), 177(14), 182(14), 208(106), 209(106), 210,23/, 234, 235( 1), 256( 1),263, 266(9), 269(9, 21, 21a, 22a, 22b, 23a), 28l(32e), 286, 287, 295(23), 299(23), 317(11 1), 3 18(111), 327(157, 159, 163), 328(165), 329(167), 335, 337, 339, 392(3), 393(3), 409(3), 410(3), 414(3), 427(3), 447(3), 449(3),

450(3), 453(3). 454(3), 459(3), 460(3), 474

Osgerby, J. M . , 125(42), 147(42), 220(110), 232, 266(11), 267(11), 268,286

O s s w a l d , G . , 134(54), 232 Ostfeld, D . , 392(12), 393(12), 399(27),

408(12, 27), 409( 12, 27), 425( 12, 27), 427(162), 440(12, 27), 442(12, 27), 446(12, 27), 447(27, 162, 163), 448( 162, 163), 449( 162), 459(244), 462(244), 464(163), 465(162, 163), 466(162, 163), 475, 479, 569(102), 579

O T o o l e , M . C,450(193),451(193), 453( 193), 454(193), 458( 193), 466(193), 480

O w e n , G . S., 43(261), 51(261), 79, 462(257, 258), 482

Owen, J . E . , 437(133),478 Overend, W. R. , 361(32),364 Ovsepyan ,T . R . , 169(85),233 Ozols, J . , 43(241), 50(241), 78

P

P a a l , C , 129,232 Paine, J. B . , III., 88(15), 99, 104(8), 111(24),

123(8), 124(8,24), 125(8,24). 127(8), 133(8), 151(8), 153(8,24), 154(8,24), 156(8), 160(8, 24), 172(8, 24), 174(8), 180(24), 182(8), 190(8), 218(8), 220(8), 221(8), 224(24), 225(24).231, 290( 1), 294(1), 297(1), 299(1), 313(1),334

Paiade G E , 3 0 , 71 Paleus, S., 54(305), 55(305, 319), 56,80, 81 Palmer, J. M . , 442( 142), 444( 142),479 Palmer, S. E . , 513(35), 514(36), 515(36),551 Palmer, T. F . , 378(49),388 Panayappan, R. , 451(215), 454(215),

462(215), Papaefthymiou, G . C , 451(218), 454(218),

460(218), 481 Pappenheimer, A. W . , Jr., 40( 134), 75 Parish, R . G . , 42(161), 48(161), 76 Park, R. , 505(34),550 Parker, M. J . , 3 10(74), 311 (74),336 Parker, J . , 305(54),336 Parkes, A. S., 29(2), 7/ Parkes, E. A . , 88, 99 P a r n i s , C , 241(20),263

Parrick, J . , 135(58),232 Pabst, A . , 535(47),55/ Pasternack, R. F . , 573(132, 135),579 Pasteur, L . , 70(392),83 Paul, K. G . , 42(157), 46(154), 55(319), 56,

67(157), 76, 81, 308(58), 313(91), 336, 337

Pauling, L . , 25(33),27, 30, 39, 40(138), 41, 42, 49(184), 58(346), 59, 67, 70(394, 395), 72, 75, 77,81,83, 418(17), 456(227),475, 481

Pauson, P. L . , 377(47),388 Pavlick, R. J . , 488(13), 490(13), 501(13),

505(13), 538(13),550 Peake, E . , 44(274), 51(274), 52(274), 79, 80 Pearson, R. G . , 431( 114), 438(114),478 Pellet ier ,P J , 38, 74 PeI l ize r ,G. , 457(238),482 Penny, E . , 52, 54, 55(279),50 Peng, S. M.,450(204a),450(204a),

465(204a),466(204a),^7 Perutz, M. F . , 30, 40( 112), 41(11), 42,

44(168),45(11),47(112, 165-169), 48( 168), 50( 112), 55( 169), 56, 58(112), 66, 67( 165-167), 68(166, 168, 382), 69(382), 71, 75, 76, 77,82

Petering, D. H . , 468(262),482 Peters, R. J . , 53, 54, 55(292),80 Peterson, E . , 44(275), 51 (275), 52(275), 79,

80 Peterson, J. M . , 54(297), 55(297),80 Petryka, Z. J . , 566(76), 568(76), 574(141),

576(141).578, 580 Pettersen, R. C. 486(7, 7a), 487(7), 535(48),

550, 551 Phillips, D . C . , 69(380),82 Phillips, L K ,443(151),479 Piciulo, P , 443( 152), 450(209),454(209),

458(240), 465(209), 466(209),478, 481 Pi lger ,T . B. G . , 43(227), 50(227), 78 Pilgrim, R . L . C , 529(45), 531(45),551 Pillinger, C. T . , 488( 14), 490( 14), 502(25),

503(25), 515( 14, 38), 520(25), 521(25), 522(25), 542(38), 550, 551

Piloty, O . , 32, 46(59), 62(59), 73, 132,232 Pinnock, H. A . , 248(40),264, 468(272),

469(272), 470(2 72), 483 Plane, R. A.,406(44),476, 573(131, 135),579 Piatt, J. R. , 50(197), 51, 77 Plieninger, H . , 105(11),257 Plotz, E . , 327(156),338 ^

P l u s c e c J . , 125(42), 147(42), 232 Pohlmann, H. P. , 488( 15), 491( 15),550 Pollinger, A . , 53, 54(293), 55(293),50 Ponnamperuma, C , 44(275), 51(275),

52(275), 79, 80 Ponomarev, G. V . , 244(29, 32), 262(29),263,

264 Poor, R. W . , 44(247), 51(247), 79, 345(11),

363 Porra ,R . J . , 297(25),335 Porter, C . C . , 58(349),81 Porter, K . R . , 3 0 , 7 / Posnyak, A. L . , 367(8), 369(8),387 Pratt, J. M . , 468(263), 471 (263), 482 Pregl, F . , 58(337), 59,5/ Prentiss, A. M . , 31(34), 72 Preobrazhenskii, N . A . , 169(85),233,

250(44), 256(44), 259(44),264 Prewitt, C. T . , 413(64), 418(64), 427(64),

432(64), 438(64), 444(64), 449(64), 476 Preyer, W . , 55(307), 57, 58(307),80 Price, R . , 104(7). 117(7), 122(7), 123(7),

126(7), 145(7), 169(84), 206(84),231, 233, 269(20), 287

Protas, J . , 398(24a), 422(23a, 24a), 423(23a, 24a), 432(23a, 24a), 433(23a, 24a), 435(23a),436(23a,24a, 13 lb), 438(23a, 24a), 440(23a, 24a),475

Puppe, L . , 44(254), 51(254, 255), 79, 395( 19), 397(19,23), 398( 19), 400( 19), 403(23, 39). 407( 19, 23), 408(48), 410( 19, 23), 411(19, 23, 39), 416(48, 66), 417(19), 418(19), 425(42, 107), 426(42, 107), 427(19, 42, 48), 429(19, 23, 119), 430(23), 431( 19, 23), 432(23. 39, 48), 433(23, 39, 48), 434(23), 435(23, 39). 436( 19, 23), 437(39, 119), 438(23), 439( 19), 440( 19, 23, 25, 39), 441(19, 23. 39), 442( 19, 39), 444( 19, 39), 445(39), 446(19, 23, 39), 447(42, 48), 449(42, 48), 462( 19), 472(19), 473( 19, 119), 474(19, 42),475,476,478

Putnam, F. W . , 60(357), 60,82 Putzer, B . , 299(36),335

Q

Quatt lebaum,W. M . , J r . , 107(18), 108(18), 231, 343(6), 363

Quelch, E. E . , 54(297), 55(297),80

R

Rajapaksa, D . , 361(32),364 Ramsay, W . N . M . , 54(297), 55(297),80,

561(31), 577 Ramsey, V. G . , 410(63), 423(63), 432(63),

435(63), 476 Rao, K. R. N.,280(32b),287 Rappoport, D. A . , 565(70),578 R a p o p o r t , H . , 134(54), 135,232, 252(52),

264, 267(13),286, 309(65),336, 564(60), 578

Rawlinson, W. A . , 311(76), 313(91),336 Reed,C.A.,89(32),/00,440,441(139),442(141),

443(141), 450(195, 196, 199), 453(191), 454(191, 195, 196, 199), 455( 199) 456( 199), 459( 196), 465( 199), 466( 199), 479, 480

R e e d , R . 1., 378(49),388 Reichert, E. T . , 55(310), 70(310).80 R e i l , S , 135(55), 232 Remer, H . , 43(245), 50(245), 79 Reuter, F . , 308(59), 336 Reyes, Z . , 451(216), 454(216),481 Rhodes, R. E . . 499(24), 520(24), 521(24),

535(24), 543(24), 544(24), 550 Rianson, W. T . , 89(32), 100 Richards, W. R . , 564(60).578 Richardson, K . , 240(14), 246(14, 38),

248(41), 258( 14), 26K 14),263, 264 Riedl , H. J . , 265( 1),286, 333(176),339 Rie tve ld ,T . , 574(143), 143 Rimington, C. J . , 32, 36, 39, 40(50), 41, 44,

45(141), 62(86), 73 , 74 , 76 , 309(68), 311(76), 318(117), 319(118), 322(139), 336, 337, 338, 561(26), 563(52), 564(52), 577

Rimmer, J . , 119(32a),231 Rinte lman ,W. L . . 375(36),388 Ripol l , D.,435( 131a),478 Rittenberg, D . , 30, 32(52), 42( 175), 48( 175),

65(12), 71, 73, 77 Roberts, G. C. K . , 47( 166), 48( 166), 66( 166),

67(166), 68(166), 76 Robertson, J. M . , 371( 19), 376( 19), 384(65),

386,387, 388 Robinson, A . B . , 309,336

Robinson, A. R . , 42( 181), 48(181), 77 Robinson, E. A . , 58(352), 60,81 Robinson, G . M . , 132(50),232 Robinson, R. , 132(50),232 Robinson, W T , 450( 199), 454( 199),

455( 199), 456(199),465(199), 466( 199), 480

Rocha-Gonsalves, A . M. cTA., 161(81), 170(81), 179(92),233, 265(6), 278(54, 55), 281(6), 285(53-55),286, 288

Roche, M . , 244(26), 262(26),263, 321(136), 338

Rochester, C. H . , 345(12),363, 367(7), 368(7), 387

Roder, A . , 451(220, 221, 222), 454(220, 221, 222).481

Rohbock, K . , 395(19), 397( 19, 23, 24, 25), 398( 19, 24, 25), 400( 19, 24), 403(24, 39), 404(40), 407(19, 23, 40, 46), 410( 19, 23), 411(19,23,39),417(19),418(19), 420( 19), 421( 19, 39), 422(23, 24, 25, 39), 423(23, 24, 25, 39, 40), 427( 19), 429( 19, 23, 39, 46), 430(23, 39, 46), 431(19, 23, 40, 46), 432(23, 24, 25, 39, 40, 46), 433(23, 24, 25, 39, 40), 434(23, 24, 46), 435(23, 39), 436( 19, 23, 24, 25, 40, 46), 437(39), 438(23, 24, 25, 40), 439(19), 440( 19, 23, 24, 25, 39), 441(19, 23, 24, 39), 442( 19, 24, 39), 444( 19, 24, 39), 445(39), 446( 19, 23, 39), 447(170), 449( 170), 452( 170), 462( 19), 464( 170), 465( 170),466(170), 472( 19), 473(19), 414,475,476,477,478,479

R o o m i , M . W . , 113(27), 115(27), 124(27), 129(49),231, 232, 254(55),264

Rosenfeld, M . , 58(358), 60,82 Rosenthal, O . , 43(243-245), 50(243-245),

78, 79 Rosscup ,R . J . , 488(15), 491(15),550 Rossi-Fanell i , A , 39, 40( 109b), 74 Rossmann, M. G . , 68(382), 69(382),82 Rothemund,P. ,33,39,40(107),7i ) 74, 86,88.

89(3, 16, 17), 90(2),99, 424( 100), 425( 100), 426( 100), 431(100), 432(100), 433(100), 447( 100), 449( 100),473(100), 477

Rougee, M . , 450(203a), 454(203a, 225a), 455Q03*),480,481

Roughton, F. J. W . , 30, 32(15), 41, 42(172), 44,48(172), 72, 75, 77

Rousseau, K. 90(35) J00 Ruccia , M . , 300(39), 331(39),335

Riidiger, W , 19,26 Rudloff, V . , 30(21), 40(109d), 67(21), 72 , 74 Rudrum, M . , 487(8), 499(8), 528(5), 533(8),

534(8), 545(8),550 Rumyantzeva, B. V . , 240(17), 250(45),

258( 17), 263, 264 Rumyantseva, V. D . . 240(17), 250(45),

251(45), 252(49), 256(45, 49), 258(17), 259(45,49), 263, 264

Rundall , F. G . , 384(66), 386(66),388 Ruppert, J . , 105(11),231 Rupprecht, G. A . , 420(77), 443(152),

450(209), 452(77), 454(209), 465(77, 209), 466(77, 204), 467(77), 477, 479,481

Russell , C. S., 562(34, 36), 566(34),577

S

S a c h , G . S., 121(34), 126(44), 146(66), 195(44), 217( 108), 232, 231 (11), 244(34), 254(56), 257(34, 56), 260(34, 56),263, 264, 265(7), 269(7), 271(7), 275(7, 38), 278(38), 281(38), 282(38), 284(38), 286, 288, 292(\2),334

Sadasivan, N . , 447( 180), 449( 180), 459(243), 480,482, 569(100), 579

Sakakibura ,S. , 309(69),336 Sales, K. D . , 450(208), 454(208),481 Sa lmond ,W. S., 21(26),26 Sams, J. R . , 423(95), 450(188a),453(188a),

454( 188a), 459(188a), 461(95),477, 480 Samuels, E . , 105(10),231 Sancovich, H . A . , 280(32a),287 San i t zke ,G . , 349(18a),364 Sano, S., 9(9),26, 244(27),263, 308(57),

309(57, 67-69), 321(132),336, 338 Sarancheck, H. J . , 61, 62(365),82 Sasada, Y . , 346(14a), 363(35),363, 364,

399(29), 468(29), 469(29),475 Sasami, H . , 43(245), 79 Sassa, S., 44(270), 51(270), 79 Satoh, F . , 111(24), 124(24), 125(24), 153(24),

154(24), 160(24), 172(24), 180(24), 224(24), 225(24),231

Sauer, J . , 8(7b),26, 236(6), 238(6),263, 281(34), 287

Saunders, J . , 111(24), 121(33), 124(24), 125(24), 135(59), 141(59), 153(24), 154(24), 155(77), 160(24), 163(59,77), 169(59), 172(24, 59), 180(24), 224(24),

225(24),231, 232, 233, 244(33), 248(33), 260(33), 262(33),264

Saunders. R. A . , 378(49),388 Sayer, P . . 432( 128b), 437( 128b),47£ Schaefer, H . . 129(48).232 Schaffer, A . M . , 378(52),388 Scha tz ,G ,69 ,&? S c h e e r , H . , 25(32),27, 423(88), 427(73),

439(88), 474(73), 477 Scheidt, W. R . , 393( 15), 395( 15), 397(15),

398(15), 399(15), 400( 15, 30, 33), 401( 15), 408(33), 419( 15), 420(77), 423( 15), 428( 15), 432( 15, 33), 433(33), 434(15, 33), 436(15, 33), 437(15), 438(15),442(141),443(15, 141, 152), 444(33), 447(15, 30), 448(30), 449(30), 450(15, 206, 209), 452(77), 454( 15, 206, 209), 456( 15, 229), 457(15, 229), 458( 15, 240), 461( 15), 463(15, 33, 258a), 465(77, 206, 209), 466(77, 206, 209), 467( 15, 77), 468(264, 266, 268), 469(264, 266, 268), 470( 15, 280) ,471(15), 472( 15, 284), 473(15), 475, 479, 481,482, 483

Schejter, R . , 40(11 la), 44(11 la), 50( 111a), 5 1 ( l l l a ) , 6 7 ( l l l a ) , 7 4

Schenkman, J. B . , 43(245), 50(245), 79 Scherer ,M ,98, / t f t f Schmid, R. , 32(42), 36(42), 42, 46(85), 72, 74 Schmidt, C. F . , 30( 14), 34(14), 72 Schmidt, R . , 108(22),231 Schneehage, H. H . , 44(255), 51(255), 79,

395( 19), 397(19, 23), 398( 19), 399( 19), 403(23, 39), 407(19, 23), 410(19, 23), 411(19,23,39),417(19),418(19), 419(75), 420(19), 421( 19, 39), 422(23, 39), 423(23, 39), 427(19), 429(19, 23, 39, 75, 119), 430(23, 39, 75), 431( 19, 23), 432(23, 39), 433(23, 39), 434(23), 435(23, 39), 436(19, 23), 437(39, 119), 438(23), 439( 19, 75), 440( 19, 23, 39), 441( 19, 23, 39), 442(19, 39), 444( 19, 39), 445(39), 446(19, 23, 39, 158), 447(75), 449(75), 451(75), 453(75), 456(75), 460(75), 461(19, 158), 472(19), 473(19, 119, 158), 474( 19),475, 476, 477, 478, 479

Schneider, F . , 410(54),476 Schneller, K . , 33(66), 73 Schodder, H . , 556(10),576 Schormuller, A . , 235(2),263 Schroeder, W. A . , 30( 18), 39, 40(22), 68, 72 Schumm,0 . ,295 , i . ?5

Schwartz, A . , 282, 283(42),288 Schwartz, S., 32(42), 36(42), 42, 46(85), 74,

75, 299(35), 320( 128),335,338, 556(15), 561 (27a), 577

Schwartz, V . , 556(11),576 Schwarz, F. P . , 306(55),336, 422( 125),47#,

432(125), 433(125),478 Schultz, J H , 32, 72 Scott, A. I., 135(56),232 Scott, C. R . , 562(40),577 Scott, J. J . , 343(9), 344(9), 345(9), 363(9),

363 Scott, R . G . , 25(32),27 Seamans, L . , 423(98), 477 Seba ld ,W. , 69(383),82 S e e l y , G . R. , 324( 149),324, 392(6),474 Seeman,C. V . , 305(5\),335 Sei tz ,G. ,49( 187a), 77 Sekuzu,I. ,315(104),3J7 Senebier, 38(40, 103), 74 Setsune, J. I., 447(178), 449( 178), 468( 178).

469(178), 470(178),480 Seyffert, R . , 43(223), 50(223), 78, 311(77,

83),JJ6 Shack, J . , 44(268), 51(268), 58(268, 349), 60,

79 Shannon, R. D . , 413(64), 418(64), 427(64),

432(64), 438(64), 444(64), 449(64), 476 Shashoua, V. E . , 43, 50(231). 78 Shaw, K. B . , 104(5, 7), 117(7), 122(5, 7),

123(5,7), 126(5,7), 127(5), 145(7), 164(84), 206(84, 103), 207(73), 23L

233,234, 250(46),264, 269(20),287 Shears, B . , 342(5), 343(5),363 Sheldon, H. J . , 31(38), 40(38), 72 She l ton ,G. , 155(78), 159(78),233, 342(4),

346(4, 14, 16). 347(4), 350(20), 351(4), 353(4), 354(4), 357(4, 29), 358(4, 29, 31), 359(29), 360(16), 361(29),363, 364, 366(3), 387, 441 {179), 449( 179), 468( 179), 469( 179), 470(179), 472(179), 480

Shelton, K. W . , 151(73), 155(73),233, 241( 18), 242(21, 23), 243(23), 244(21), 246(21, 36, 38), 258(21), 261(21, 23), 262(23),263, 264, 327(162), 329(162), 339

Shemin, D . , 30, 32(52), 37(93), 39, 41, 42( 175), 46(92, 93), 48(175), 65(12, 92, 93), 71, 73 , 74 , 77

Shergalis, W . , 89, 92, 96,100, 572(123),579

Sherma, J . , 554(6), 556(6),576 Shimazono, N . , 561(32), 564(32),577 Shingu ,T. , 9(9),26, 244(27),263, 321(132),

338 Shore, V C , 69(380),82 Shulga, A. M . , 367(8), 369(8),387 Shulman, R. G . , 278(54), 285(53, 54),288 Shutt leworth,R. , 105(10), 2 J / S idd iqu i ,Z V , 440(145),479 Sidwell , A. F . , 44(267), 51(267), 79 S i e b e r , N . , 55(308),<S0 Siedel, W . , 14,26, 87,95,97,99, 149(70),

233 Siegelman, H. W . , 19(23),26 Sievers, G . , 293, 295(13),334, 562(39),577 Simmonds, D. H . , 42(214), 64(372), 69(372),

78, 82 Simon, S R , 47( 165, 166), 48( 166), 66( 165,

166), 67(165, 166), 68(166), 76 Simone i t ,B . R. , 538(51),551 Singer, R. B . , 30( 14), 34(14), 72 Singer, S.J. ,30(18), 72 Singh, R . , 347(17), 363 Sinyakov, G. N . , 367(8), 369(8), 387 Skapski, A . C , 444(155),479 Skeggs, L . , 54, 55(296),80 Sklar, L . , 92(38), 94(38), 98(38), 100 Slade, E. F . , 47( 167), 66(167), 76 Slama, J. T . , 309,336 Slater, E . C , 43(217), 78 Slater, G . , 573(130),579 Sligar, S . G . , 416(72), 476 Smith, D. B . , 40(137), 75 Smith, D . W . , 457(236), Smith, E. L . , 40, 43, 50( 11 la), 51(111),

67(111), 74, 75 Smith, G. D . , 522(43), 538(52),551 Smith, H . W . . 309(65),336 Smith, K. ,427( 103a),477 Smith, K. M . , 107(13), 119(32a), 127(44a),

145(30), 147(68b), 156, 161(81), 170(81), 179(92), 195(99), 206(102), 211, 216( 107), 224( 102), 226( 102), 231, 233, 234, 242(24), 252(50), 255(57, 59), 257(24), 262(24), 263, 264, 265(6), 274(29), 275(30), 277(3 la), 278(29, 31a, 41a, 45b, 54, 55), 281(6, 29, 3 l a , 41, 41a), 283(45b), 284(45b, 56), 285(53-55),286, 287, 288, 302(48), 329(48), 332(172, 173),335,339, 367(6),387, 402(36), 406(43), 409(43), 425(43, 108),

426(43, 108), 427(36, 108), 429(43, 112), 430(112), 431(112, 113), 437(113), 453(43),475, 476, 477, 478, 572(128), 579

Smith, L . , 43, 50(238, 239), 78 Smith, M. L . , 309(71), 31 1(71), 312(71),

315(71), 316(71),336 Smith, P. D . , 420(77), 421(77), 422(83, 84),

423(84, 89), 432(125), 433(125), 437(125), 447(78, 83, 84, 89), 452(77, 78, 83, 84, 89), 458(84), 464(78, 83, 84), 465(77, 83, 84, 89, 260), 466(77, 83,84, 89, 260), 467(77, 84), 468(84),477, 482

Smith, S. G . , 224( 113), 225(113),234, 280(32a, 32b), 283(43), 284(43), 287, 288, 561(2a),577

Smythe, G. A . , 145(62), 147(68a), 151(71), 184(62), 186(71), 215(62), 216(62), 218(60), 220(71), 221(71), 223(62), 224(90, 116), 228(90, 116), 232, 233, 234, 268( 19), 269( 19), 287, 309(71), 311 (71), 312(71), 313(102), 315(71), 316(71),336, 337, 451(194),453(194),454(194), 461(194), 480

Snader, K . M . , 563(54),578 Snyder. L . C, 43(218), 50(218), 78 Snyder, L. R. , 554(7), 556(7), 558(17),576,

577 Snyder, W. D . , 488( 16), 489(16), 491(16),

533(16), 567(88),550, 578 Sono, M.,562(43a),577 Solov 'ev, K . N. ,89,100 Sono, M . , 302(43), 303(49), 305(49), 309(49),

313(43),J35 Sorby, H . C . , 33, 57,73,81 Sorensen, N. A . , 64(379), 69(379),82 Soret, J . L . , 49, 77 Sor re lKT N ,450(205),451(219),454(205,

219), 458(205), 460(219),43/ Sovocool , G. W . , 447( 160), 448(160),

449( 160), 465( 160), 466( 160), 479 Spackman, D. H . , 42(177, 178), 48(177, 178),

77 Sparatore, F . , 302, 329(47),335 Spaulding, L. D . , 423(86), 450(86), 454(86),

477 Spiers, D. B . , 370(\6),387 Spilburg, C. A . , 431(120), 432(120),

468(262),478, 482 S p i r o , T . G . , 423(85),477 Srivastava, T. S., 399(27), 400(31), 408(27),

440(27, 137, 138), 441(137), 442(27, 142), 444(142), 446(27, 137, 138), 447(27, 161),448(161),451(210), 454(210), 465( 161), 466( \6\),475,479, 481

Stanienda, A . , 473(285),483 Stapfer, C. H . , 133(51),232 Staunton, J . , 329(169),339 Steckhan, E . , 129(48),232 Stedman, R. J . , 112(26),231, 318(115),337 Stein, P . , 423(85),477 Stein, W. H.,42,48(177, 178), 77 Steinhardt, J . , 58(347), 61, 66 ,5 / Stenkamp, R. E . , 432( 128a),434(128a),478 Stephen, E . , 88 ,99 , 372(21),387 Stephenson, G. F . , 43(264), 51(264), 79,

269(24), 257, 570(111), 579 Stern, A . , 4(6),2d, 324(147, 148),JJ5,

392(4), 393(4), 409(4), 414(4), 427(4), 447(4), 449(4), 450(4),474, 494(21), 496(21), 509(21), 510(21),550

Stevens, T. S., 105(10),2J/ Stewart, M . , 298(32), 299(32), 313(32, 96),

335,337 Stich, W . , 559(23), 560(23),577 Stimson,C ,356(26c) , i64 S t i t t ,F . , 49(183), 77 Stojanac, N . , 125(42), 147(42),232 Stokes, G . G . , 70(390), 82 Stokvis, B. J. E . , 36(83, 84), 73, 74 Stoll , A . , 32(61), 39, 7 i , 324(146, 150).

325(151), 326, JJ5 , 392(5), 393(5), 409(5), 450(5), 453(5),474

Stoll , M S , 574(138, 139, 140, 142) 576(138, 139, 140, 142), 580

Stone, A . , 363(36),364 Stoppa, H . , 419(22), 422(22),475 Storm, C. B . , 535(49),55] Stotz, E . . 42(207), 77, 311(81), 313(92, 93,

94),336,337, 564(63, 64), 578 Strain, H . H . . 25(31),27 Strandberg, B. E . , 67(380), 69(380),82 Strangeways, D. H . , 54(297), 55(297),50 Straub, D. K . , 440(171), 447(171), 449( 171),

450( 198), 451( 198), 453(171), 454(198), 459( 171. 246), 460( 171), 461, 468( 198), 179, 480, 482

Streibl, M . , 542(59),551 S t r e l l , M , 8 , 2 6 Strittmatter, R . , 43, 50(240, 241), 78 Strosher, M . , 501(32), 503(32), 520(32),

522(32), 550 Studier, M. H . , 25(31, 32),27 Stults. B. R. , 442(144),479 Stynes, D. V . , 468(261, 273, 274), 469(273,

274), 470(273, 274),482, 483 Stynes, H . C . , 468(261),452 Subba Rao, B . C . , 268(18), 287 Suckling, C. J . , 278(41a), 281(40, 41a),288,

323(144), 338 Sugimoto, N . , 454(223), 457(223),481 Sullivan, J. F . , 400(32), 401(32), 402(32),475 Summerville, D. A . , 463(258a),452 Supphayen, D . M . , 280(32b),287 Surgenor, D. M . , 58(362), 60,52 Suslick, K. S., 457(232, 232a),481 Suzuki , K . , 409(50), 435( 130), 440(50),

441(135),476, 478 , 569(101),579 S v e c , W . A . , 25(31, 32),27 Sweeney. A . , 342(4), 346(4), 347(4, 18),

351(4, 21), 353(4), 354(4),363, 364, 447(179), 449( 179), 468(179), 469(179), 470( 179), 472( 179),480, 544(63), 551

Swift, W . , 440( 171), 447(171), 449( 171), 453(171), 459(171), 460(171),479

Swinton, P. F . , 472(282),483 Syal , S K ,346(14a),J6J Sydow, V . L . , 239,263 Szutka. A . , 571(117),579 Szymanski, T . , 457(237), 468(237),481

T

Tagawa, K . , 55(321), 56 ,5 / Tahenaka, A . , 346(14a),363 Takemori , S., 43, 50(230), 78 Takemoto, J . , 440( 175), 447( 175), 449( 175),

480 Takenaka, A . , 363(35),364, 399(29), 468(29),

469(29), 475 Tanford, C . , 42( 160), 46( 160), 48(160), 76 Tang, S. C, 451(218, 224), 454(218, 224),

460(218, 224),481 Tarlton, E. J. 169(87), 224(87), 225(87),233,

265(3), 273(3),286, 319(120),337 Tasset, E . L . , 442(144),479 TaubeR. , 377(48),388 Taylor, D. N . , 313(100), 315(100),337 Taylor, G. A . , 392(13), 393(13), 409(13),

425( 13), 440(13), 442(13), 446(13), 475

Taylor, J. F . , 58(335), 58 Taylor, K. T . , 378(50), 379(50),388 Tcherniac, J.,374(32),388 Teichmann, L . , 31, 72 Terrell , R. J . , 345(12),363, 367(7), 368(7),

387 Terry, W . G . . 134(53),232 Theophanides,T. , 401(35),475 Theorell , H . , 30, 42(155, 157), 43(236),

45(148), 46(153, 154, 155),48(157), 50(196, 236), 55(9, 319), 56, 57(155), 58(350), 60, 67(157), 71, 76, 77, 78,81, 309(62, 63), 447( 181), 449(\$\),480

Thomas, A. L . , 374(27), 375(40), 379(27), 387,388, 393(14), 475

Thomas, D. W.,89,100, 416(70), 447( 182, 183), 449(182, 183),476, 480

Thomas, J . , 374(31),388 Thomas, K . M . , 351(24a),564 Thomas, R . , 43(253), 51(253), 79, 399(28),

410(59), 421(28), 427(59), 429(28), 430(28), 447(59), 449(59),475, 476

Thonger, E . , 9(9),26, 244(27),263, 321(132, 135), 322(140),338, 501(58), 535(58), 541(58), 551

Thorne, E. J . , 87, 95(6), 96(6), 97(6), 99 Thorp, R . , 447( 166), 448( 166), 449( 166), 479 Thorpe, A . , 451(215), 454(215), 462(215),

481 Thudichum, J. L. W . , 35, 75, 297(24),335 Timkovich , R , 420( 104), 425( 104), 426( 104),

477 Tooth, B. E . , 32(49), 73 T o n n , B . , 422(111), 423(111), 478 T o n n , M . , 451(214), 454(214), 461(214), Torrens, M. A . , 459(246), 461 (246),482 T o s s i , L , 42(213), 78 T o w i l l , R . , 574(137, 142), 575(137), 576(142),

580 Townsend, C. A . , 135(55),232 Traylor, T. G . , 327(160, 161),339, 450(203),

454(203, 226), 455(203), 458(226), 480, 481

Treibs, A . , 33, 43, 44(62), 50(246), 51(62, 246, 248, 262, 263), 73, 79, 88, 89, 95(11), 96,97,98,99, 107(15), 108(15,22), 112(15), 123(37), 124(39), 127(39), 143(37), 231,232,233, 266(10), 277(31), 331(170),286, 345(10),363, 392(7), 393(7), 409(7), 416, 429, 432( 126), 434( 126),435(126), 437(71),

440(71), 442(71), 450(188), 453(188), 474, 476, 478, 480, 486(1), 488(9), 490(9), 505(1), 506(1), 507(1), 509(1), 517(9), 520(9), 536(1), 539(53), 542(1), 545(9),550, 551

Trochagrimshaw, J . , 346( 14b),363 Tschamber, T . , 356(23, 27), 357(27),364 Tschirch, A . , 38, 39, 40(101), 74 T s i n , T . B . , 423(95), 450( 188a), 453( 188a),

454( 188a), 459( 188a), 460(95), 477, 480 Tsutsui, M . , 392(12, 13), 393(12, 13),

399(27),408(12, 27), 409( 12,13,27,50), 435,440(12, 13, 27, 50), 441(135), 442(12, 13, 27), 446(27), 447(27, 161, 162, 163),448(161, 162, 163)449(162), 464( 163), 465( 161 -163), 466( 161 -163), 475,478, 479,569(101, 102), 578

Tsvirko, M ,89,100 Tswett, M . , 39, 40(122), 70(388), 75, 82 T u e y , G . A. P . , 384(65, 66), 386(65, 66),388 Tulinsky, A . , 43(257), 251(257), 79,

420(104), 425(104), 426(104), 477 Turner, D. R . , 457(238),482 Tynan, E . C , 533(46), 534(46),557

U

Unsworth, J . F . , 127(44a),232 U r a t a , G . , 37(95), 74 U l l m a n , E F , 89(31), 100

V

Valasinas, A . , 125(41), 126(41),232, 316(108), 337

Valenta, Z . , 8(7b),26, 236(6), 238(6),263, 281(34), 287

Vallee, B. L . , 431(120), 432(120),478 van de Broek, P. , 246(35), 248(41),264 van K a a m , J . , 404(40), 407(40), 423(40),

431(40), 432(40), 433(40), 436(34, 40), 438(34, 40), 475, 476

Vannotti , A , 3 9 , 40(127), 75 Van Slyke, D D , 39, 40(123), 75 Varadi , V . , 95(42), 100 569(104), 572(104)

579 Vaska , L . , 454(225), Vaughan, G. B . , 533(46), 534(46),551

Velapoldi , R. A . , 424(135), 435(130), 441(135),478, 569(101),579

Vel ick , S. F . , 43(240), 50(240), 78 Venerable, D . , 447( 166), 448( 166), 449( 166),

479 Venteicher, R. F . , 421(117), 429( 117),

430(117),431(114, 120),432(117, 120), 478

V e n t u r e G . C . , 573(132), 579 Verdei l , 40(133), 75 Vernon, L . P . , 392(6),409(6),474 Vestling, C S , 58(335, 349), 60 ,5 / Vierordt, K . , 38,40(118, 119), 75 V i o h l , P , 156(80) 160(80), 169(80),

204(101), 233,234 Viscont ini , M . , 112(25),231 Viswanatha, V . , 346( 14b), 363 Vlaes, F , 49, 77 Vohwinkel , F . , 409(50), 440(50), 441(135),

476,478, 569(101),579 Voigt, H . , 88(13), 99, 302(44), 333(44),335,

447(184), 449(184), 480 Voldodarskaya, G. Y . , 252(48), 256(48),264 V o l ' K e n s h t e i n , M V , 486(3), 507(3),

539(3), 550 V o l k e r , W . , 313(97),337 Vollmann, H . , 374(29), 375(29), 337(29),

379(29), 387 V o l z , H . , 8(7b),26, 236(6), 238(6),263,

281(34), 287 von d e r H a a r , F . , 502(27), 550 von der Weid , E . , 374(33),388 von Kol l ike r , A , 38, 40( 114), 75 von Kruger, F . , 58(336, 343), 59,81 von Maltzan, 90(37),/tftf von M i s e s , R , 525(44), 551 von Nenck i , M . , 55(303, 308),80 von Rebay, A . , 384(62, 63),388 von Seemann, C, 55(313), 56(313),

244(28), 263 von Zeynek, R., 58(341), 59,81 Vouschne, H. G . , 349( 18a),364

W

Wagner, G. C . , 450(202), 454(202), 455(202), 458(202), 480

Wagniere ,G. , 43(218), 50(218), 78 Walach, B . , 87, 99, 206(93), 233

Waldenstrom, J . , 32. 36, 39, 40(40), 63, 69(369), 72, 82, 319(124), 337

Walker, B. S., 54, 55(301),80 Walker, F. A . , 444( 156), 461(251), All,478,

479, 482 Walker, J . M . , All,478 Wallace, W. H . , 454(204), 457(204),480 Wallenius, G . , 30(23), 42(23), 45(23), 46(23),

72 Walter, J . A . , 347(7),363 Walter, R. I., 573(134),579 Wang, J. H . , 42, 77, 457(234),481 Warburg, O . , 49, 55(310, 311), 56, 77, 80,

310, 311(79), 313(86, 88),336 Warburton, D . , 265(4), 274(4),286 Ward, D . , 350(20),364 Ward. A. D . , 87, 90(8),99 Warme ,P . K . , 563(46),577 Wasley, J. W. F . , 224(114), 225(114), 234 Wass, J . , 177(89), 224(89), 225(89), 226(89),

233, 244(30), 257(30, 61)263, 264, 273(26), 275(26, 39), 281(39), 282(39), 283(39),287, 288, 304(52), 320(127), 321(137),335, 338

Wasserman, A. R . , 43(238), 50(238), 78 Watanabe, E . , 363(34, 35),364, 451(213),

454(213), 459(213), 460(247), 461(213), 481

Watenpaugh, K. D . , 432( 128a), 434( 128a), 478

Watson, C. J . , 32(42), 36, 39, 40(130), 67(380), 72 , 75, 82 , 298(29), 335, 566(76), 568(76), 574(141), 576(141), 578, 580

Watson, H . C . , 69(380),82 Wayland, B. B . , 444( 153), 450(207),

454(207), 458(207), 465(207), 466(207), 468(265, 278), 469(265, 278), 479, 481, 482,483

W e b b , L . E . , 50(219), 78 Webb, N. W . , 195(97),234, 244(31), 251(31),

252(31, 51), 254(54), 256(31), 259(54), 264, 281(33),287

Week, D. D . , 397(23), 407(23), 410(23), 411(23), 422(23), 423(23), 430(23), 431(23), 432(23), 433(23), 434(23), 435(23), 436(23), 438(23), 440(23), 441(23), 446(23),475

Wecker, G.,302(43a),335 Wei , P. E . , 419(76),477, 494(6), 509(6),

518(6), 520(6), 542(6), 550, 511 (116), 579

Weiss, C , 378(51),388 Weiss, F. T . , 376(41, 43),388 Weiss, H . , 69,52 Weiss, R. ,385,J&S, 398(25a), 422(25a),

423(25a), 475 Weissbluth, M . , 423(94),477 Wells , I . C, 30(18), 72 Wenderlein, H . , 494(21), 496(21), 509(21),

510(21),55<9 Werner, S., 69(386),82 Weschler, C. J . , 443( 149), 450( 197),

454(197), 455(197), 465(197), 466( 197), 479,480

West, P. J . , 135(58), 135 West, R . , 32(52), 73 Whalley, M . , 370(12, 14, 16), 371(18),

372(21), 387 Whelan, J.,254(55),264 White, W. I., 569( 105), 573( 131),579 Whitlock, H. W . , Jr., 88(14), 99, 115(29b),

117(31), 123(31), 127,2J/,410(61), 421(61), 427(61), 447(61), 449(61), 468(271), 470,476, 483

Whitten, D. G . , 44(247), 51(247), 79, 345( 1 \),363, 400(30), 423(92), 437( 132), 439(132), 447(30, 92, 160, 164), 448(30, 92, 160, 164), 449(30, 160), 452(92), 464(92, 164), 465( 160), 466( 160),475, 477,478,479,480

Wicholas, M . , 450(21 la), 454(21 la),481 Wickliff , J L 327(I58) ,JJ9 Wickwar , H . , 345(12),363, 367(7), 368(7),

387 Wiedemann, H . , 556( 14), 565( 14),577 Wightman, R. H . , 329(169),339 Wilchek. M . , 564(66),578 Wilkerson, C. J . , 450(201), 454(201).

455(201), 280 Wilkinson, G . , 416(18), 418(18). 439(18).

458(18), 473(18),475 Will iams. A. E . , 378(49), Will iams, G E , 572( 127), 579 Will iams, K. W . , 563(51), 577 Williams, N. R . , 115(30), 125(30), 126(30),

127(30), 174(88),231,233, 265(2),286 Will iams, R. G . , 43(215), 78 Will iams, R J P , 42, 49( 185), 50, 51, 77,

451(220, 222), 454(220, 222). 457(236). 481

W i l l s o n . C . D . , 134(54),232, 267(13),286

Wills ta t ter ,R. , 14,26, 32,33,38,39,40(61), 53, 54, 55(293, 309), 73, 80, 321(133), 324(146, 150), 325(151), 326, 392(5), 393(5), 409(5), 450(5), 453(5), 474, 488(17),491(17),550

Wilson, C . G . , 309(65),336 W i n a n s , C . F . , 108(21),231 Winkelman, J. ,573(130, 133), 579 Winkler , F . , 87, 95, 97,99, 149(70),233 Winter, M . , 354(26, 355(26), 360(26),364 W i s e , C . D . , 58(353), 60,81 W i t h , T . K . , 14, 18,26, 32(51), 7J, 560(26),

561(22), 562(42, 43), 564(59), 566(43), 577, 578

Wittmann-Liebold, B . , 30(21), 67(21), 72 Wolberg, A . , 473(286),483 W o n g , C . P. , 421(116, 117), 422(116),

429(116, 117), 430(116, 117), 431(116, 117), 432( 116, 117), 433(116), 436(116),

478 Wong, J . , 440( 139), 441 (139),479 Wong, K. L. ,450( 188a), 453( 188a),

454( 188a), 459( 188a), 480 Woodrow, G . N . , 563(47a),577 Woodward, I., 371 (19), 376( 19), 387 Woodward, R. B . , 8 , 2 6 , 177, 195(74),233,

236(6), 238(6),263, 281(6),287, 539(54), 55 L 558(18), 577

Wootton, I. D. P. . 54, 55(297),80 Wright, J . M . , 380(54),388 Wyman, J . , Jr., 39, 40( 109), 41, 47, 49(184),

66,74, 77

Y

Yagodina, L. A . , 383(60a), J&S Yamamoto, A. ,443( 151),479 Yamamoto, H . , 563(47a),577 Yamanashi, B. S., 43(258), 51(258), 55(321),

56,79,81 Yamane, T. , 278(54), 285(53, 54),288 Yamazaki , I., 300(40-42),335 Y a u , J . C . N . , 439(134),478 Yee, S., 442(141), 443(141),479 Y e n , T. F . , 499(24), 520(24), 521(24),

533(46), 534(46), 535(24), 543(24), 544(24). 550, 551

Yonetani, T . , 41, 43(232, 233), 45, 50(232-234), 55(233), 56, 76, 78, 297(34), 298,

313(33),335, 563(47, 47a, 48, 50), 564(50), 567(50). 569(50),577

Yong, F C, 43, 50(230), 78 York , J. L . , 43, 50(225), 78, 291(6), 292(6),

294(6), 295(6), 296(6), 298(6), 299(6), 300(6), 301(6), 302(6), 303(6), 313( 100), 315(100), 334, 337, 564(65), 568(93), 578

Yoshida, M . , 561(32), 564(32),577 Yoshida, Z . , 363(34, 35),364, 399(29),

427( 178), 440( 175), 447( 175, 178), 449( 175, 178), 451(213), 454(213, 223), 457(223), 459(213), 460(247), 461(213), 468(29, 178), 469(29, 178). 470(178), 475,480,481,482

Y u , C . I.,48(171), 61(171), 76 Y u , N. T . , 423(86), 450(86), 454(86),477 Yuan , M . , 562(36),577

Z

Zaleski , J . , 55(303),S0 Zane t t i ,C . U . , 104,231 Zass. E.,427( 103a),477 Zeile, K . , 33(73), 56, 73, 294(19), 300( 19),

308(58). 309(64),335,336, 450(188), 453(188), 454(188),480

Zeller, M . V . , 423(97),477 Zerner, M.,431( 1 \5),478, 544(61),551 Zinoffsky, O . , 39, 40(121), 52, 53, 54, 75, 80 Zinsmeister ,R. , 108(22), 123(37), 127(37).

143(37), 231 Zscheile, F. P. , 44(267), 51(267), 79 Zuckerandl, E . , 70(394, 395),83 Zuelzer, W, W . , 42( 181), 48(181). 77 Zuntz, N . , 38, 40(116), 75 Zweig, G . . 554(6), 556(6),576

Subject Index

A

Acetic acid, solvent for porphyrin retalia- tion, 405

Acetoacetic acid derivatives, nitrosation, 107

Acetonedicarboxylic esters, nitrosation, 107 Acetoxymethylpyrroles, synthesis, 149 Acetoxyporphyrinogens, 277 Acetyl acetonates, for porphyrin metalla-

tion, 405 ,407 N-Acetylcorroles

electronic spectra, 362 nmr spectra, 361 synthesis, 361

4-Acetyldeuteroporphyrin diethyl ester, synthesis, 259 3-Acetyl-8-ethyldeuteroporphyrin dimethyl ester, synthesis, 259 Acid lability, metalloporphyrins, 418 Acylation, oxophlorins, 277 N-alkylcorroles, 357-361

electronic spectra, 358 mass spectra, 360 nmr spectra, 357 rearrangements, 358 synthesis, 357 X-ray structure, 358

3-Alkyl-2,4-pentanediones, 104 meso-Alkylporphyrins, synthesis, 90

N-alkyl-meso-tetraphenylporphyrins, 354-357

electronic spectra, 355 nmr spectra, 354 preparation, 354

Alkyls cobalt, 470 iron, 470

Allomerization of chlorophylls, 326 Alumina, porphyrin chromatography, 567 Aluminum porphyrins, 429 m-oxo dimers, 429 Ammonium mucate, pyrrole synthesis, 129 Amyl nitrite, nitrosating agent, 107 p-Anion radicals, phthalocyanins, 377 Antimony porphyrins, 436, 439 Antimony octaethylporphyrin, X-ray struc- ture, 437 Aplysioviolin, nomenclautre, 20 Apomyoglobin, reconstitution with Yb

mesoporphyrin, 431 Arsenic porphyrins, 436, 439 N-Arylcorroles, 360 meso-Arylporphyrins

b-substituted, 89 synthesis, 88

Aroyldipyrrylmethanes, 90 Atropisomers, 89 Azafulvenium ions, in porphyrin synthesis,

93

electrophilic attack, 271 nomenclature, 14 oxidation to bilenes-/?, 255 5-oxo,255 Bilatrienes, nomenclature, 14 Bilatrienes-abc from biladienes-abc, 246 Bilenes, nomenclature, 14 Bilenes-a, from bilenes b, 244, 253 Bilenes-b

from bilanes, 255 copper promoted cyclization, 252 cyclization to porphyrins, 249-257 1,19-dicarboxylate esters, cyclization with orthoformate, 257 cyclization to porphyrins, specific examples, 260 l,19-dimethyl,256 from 1,19-dimethylbiladienes-rtc, 258 from dipyrrylmethanes, 249 electronic spectra, 273 l-formyl-19-methyl,256 from 5-formyldipyrrylmethanes,

250 1-methyl, 256 properties, 249 rearrangement to bilenes-a, 249,

253 1-thioformyl, 257

Bilin, nomenclature, 15 Bilirubin, nomenclature, 18 Biliverdins, nomenclature, 17 Biological markers, 486 Biosynthesis

heme, 45, 65, 317 chlorophyll, 36

2-2'-Bipyrroles, nomenclature, 3 N,N-bisethoxycarbony lmethylporphyrins

nmr spectra, 350 synthesis, 350

Bismuth porphyrins, 439 Bitumen, porphyrin occurrence, 517 Bohr effect, 47 Books, in porphyrin field, 38, 393

Boron octaethylporphyrin [(B2O(OR)2(OEP)], X-ray structure, 399

Boron porphyrins, 429 Brominative decarboxylation, pyrrole car-

boxylic acids, 154 5-Bromo-5'-bromomethylpyrromethene,

conversion to biladienes-ac\ 242

6-Azaindole, precursor of porphobilinogen, 135

Azaporphyrins, 365-388 from biladienes-ac, 249 Azines, pyrrole precursors, 132

B

Bacteriochlorin(s), nomenclature, 4, 13 Bacteriochlorophyllgg, nomenclature, 25 Bacteriopheophorbide a, nomenclature, 13 Bacteriopheophytina, nomenclature, 13 Barium porphyrins, 426 Basicity monazaporphyrins, 367 N-substituted porphyrins, 344, 347 Benzonitrile, solvent for porphyrin metalla-

tion, 405,407 Benzoyl chloride, Vilsmeier formylation of pyrroles, 146 Benzyl 3-(2-methoxycarbonylethyl)-4,5- dimethylpyrrole-2-carboxylate, synthesis, 115, 116 Benzyl 4-(2-methoxycarbonylethyl)-3,5- dimethylpyrrole-2-carboxylate, synthesis, 114 Benzyl 3-(2-methoxycarbonylethyl)-4- methoxycarbonylmethyl-5-methylpyr- role-2-carboxylate, synthesis, 113 Benzyl pyrrolecarboxylates, hy-

drogenolysis, 145 Beryllium porphyrins, 425 Biladienes, nomenclature, 15 Biladienes-ac

to azaporphyrins, 249 from 5-bromo-5'-bromomethylpyr- romethenes, 242 conversion to monoazaporphyrins, 366 copper promoted cyclications, 238 cyclization to porphyrins, 238-249 to 1-methyltetradehydrocorrins, 246 from 5-methyl-5-unsubstituted

pyrromethanes, 242 properties, 244 synthesis, 238, 242 Bilanes from bilenes-b , 255 dehydrogenation to bilenes-, 255 electronic spectra, 273

1-Bromo-19-methylbiladienes, cyclization to porphyrins, specific examples and experimental details, 261 Bromoporphyrins, hydrogenolysis, 282 t-Butyl hypochlorite methylpyrrole chlorination, 148, 150, 159 oxidation of bilanes to bilenes-6, 255 oxidation of methylpyrrylketones, 269 t-Butyl pyrrole carboxylates, removal of t-butyl group, 153

nomenclature, 7 preparation, 327

Chlorin e6

nomenclature, 7 preparation, 326

Chlorinp6, nomenclature, 7 Chlorobium chlorophylls

nomenclature, 25 synthesis of related porphyrins, 257

Chlorocruoroporphyrin, see Spirographis

porphyrin Chloroethylporphyrins, 281 Chlorohemin, synthesis, 33 Chloromethypyrroles, synthesis, 148 5-Chloromethylpyrrylketones, 269 Chlorophyll(s)

allomerization, 326 biosynthesis, 36 conversion to porphyrins, 324-329 nomenclature, 24

structures, 510 Chlorophyllin, 325 Chloroporphyrine4, nomenclature, 7 Chloroporphyrinp6, nomenclature, 7 meso-Chloropyrrylmethene, 220 Chromatography of porphyrins and metal- loporphyrins, 553-580

carboxyl containing porphyrins, 560 choice of method, 554 column, 563 high pressure liquid, 492, 558, 574 metalloporphyrins, 419 paper, 559, 565

precautions, 557 thin layer, 562

Chromium (acac)3, 403 Chromium porphyrins

oxygenation by dioxygen, 440

synthesis, 440 Cis and trans effects, 465 Cobalt N-methyl-ra^so-tetraphenylporphy-

rin, X-ray structure, 356 Cobalt porphyrins

dioxygen adducts, 468 ligand exchange, 452, 468 metal alkyls, 470 N-Co methylene bridged, 350 redox chemistry, 452 synthesis, 449, 468

Coboglobin, 456 Colloquia, in porphyrin field, 40

C

Cadmium porphyrins, 426 Calcium carbonate, chromatographic sup-

port for porphyrin chromatography, 556 Calcium porphyrins, 426 Capped porphyrins, 455 2-Carbethoxy-4-alkyl-3,5-dimethylpyr-

roles, 104

N-Carbethoxyglycine esters, pyrrole pre- cursors, 134 meiso-Carbon atom, nomenclature, 3 Carbonyl complexes hemes, 457 iron porphyrins, 457 osmium porphyrins, 463, 466 rhodium porphyrins, 471 ruthenium porphyrins, 463, 466 Carbonyl diimidazole, 332 Catalytic hydrogenation, iodopyrroles, 124 Cellulose, column chromatography of por- phyrins, 563 tic of porphyrins, 562 Ceric ammonium nitrate, oxidation of dipyr- rylmethanes to pyrrylketones, 220 Cerium porphyrins, 424 Charge transfer bands, metalloporphyrins, 417 Chemical fossils, 486 Chlorin(s)

N,N-dimethyl, 353 nomenclature, 4, 13

removal from porphyrins, 90 mpso-tetraphenyl, 89

N,Af,AMrimethyl, 353 Chlorin, 5

nomenclature, 8 Chlorin e4

Cytodeuteroporphyrin

preparation, 310 structure determination, 310

synthesis, 240 Cytoporphyrin, nomenclature, 11

Conferences, in porphyrin field, 40 Coordination-types of metalloporphyrin, 396 Copper deuteroporphyrin dimethyl ester,

Vilsmeier formylation, 302 Copperetioporphyrin I, synthesis, 239 Copper porphyrins, 471

electronic spectra, 472 redox chemistry, 473 synthesis, 449

Copper uroporphyrin, 33 Coproporphyri n(s)

chromatography, 560 nomenclature, 7

Coproporphyrin I preparation, 320 synthesis, 211

Coproporphyrin II from protoporphyrin, 329

synthesis, 246 tetramethyl ester synthesis, 248, 258 Coproporphyrin III preparation, 320 tetramethyl ester synthesis, 226, 228 Coproporphyrin IV synthesis tetramethyl ester synthesis, 257, 260, 275 Coproporphyrinogen III, enzymatic decar- boxylation, 280 Coproporphyrin IV, enzymatic decarboxy- lation, 323 Corphin, nomenclature, 21 Corroles

N-acetyl, 361 N-alkyl, 357-361 N-aryl, 360 N,N-dialkyI, 359

N-methyl, X-ray structure, 358 nomenclature, 19 Countercurrent distribution, porphyrins, 584 Cruentine, 34 Cryptopyrrole, 104

synthesis, 117 Crystallization of porphyrins, hemes, and

heme proteins, 55, 585 Cyanovinyl, protecting group for formylpyroles, 146 Cyanovinylpyrroles, properties, 147 Cytochrome c, crystallization, 56

D

Dealkylation, N-Substituted porphyrins, 347 Decarbonylation, formylpyrroles, Wilkin- son's catalyst, 163 Decarboxylation

enzymatic, 280, 323 uroporphyrinogen I, 280

Dehalogenation, catalytic hydrogenation of halopyrroles, 154

Dehydration, hematoporphyrin, 298 Deiodination, iodopyrroles, 124 Demetallation of porphyrins, 417 Deoxophylloerythroetioporphyrin

nomenclature, 12 synthesis, 252, 256, 262

8-Desmethyldeuteroporphyrin, see

Cytodeuteroporphyrin Deuterated porphyrins, 285, see also Iso-

topically labelled porphyrins Deuterohemin

dimethyl ester, Vilsmeier formylation, 302 electronic spectrum, 294 from protohemin, 295 purification, 295, 465

pyridine hemochrome, electronic spec trum, 295 Deuteroporphyrin

chromatography, 296 diacetyl, 226, 294, 300 dibromo, 294 diformyl, 302

dihyroxymethyl, 294 dimethyl, 228, 332

dimethyl ester electronic spectrum, 295 synthesis, 243, 262

dipropionyl, 294 dipropionyl-hemin, 300 electronic spectrum, 294 formyl vinyl, 302

isomer se paration, 562 hydroxyethyl v inyl, 292 nitro, 294

nomenclature, 11 preparation, 295 Diacetyldeuterohemin purification, 301, 564 pyridine hemochrome, electronic spec- trum, 300 synthesis, 300 Diacetyldeuterohemin dimethyl ester, 301 demetallation, 301 Diacetyldeuteroporphyrin dimethyl ester, 259, 300 synthesis, 226, 250, 259 3,7-Diacetyldeuteroporphyrin III, synthesis, 240

Diagenetic r eactions of p orphyrins, 505, 53 6 N ,N-Dialkylcorroles

mass spectra, 360 nmr spectra, 360 synthesis, 359

/V, N-Dialkylporph yrins basicity, 347 dealkylation, 347 electronic spectra, 349 mass spectra, 349, 355 nmr spectra, 348, 354

synthesis, 346, 352, 354 Diatomaceous earth, porphyrin chroma- tography, 567 Diazabenzoporphyrins, synthesis, 384 Diazaporphyrins

electronic spectra, 369 metal complexes, 369 synthesis, 369

Diazomethane, reaction with protohemin, 213

Diborane reduction of acylpyrroles, 127 reduction of formylpyrroles, 271

reduction of pyrrylketones, 271 b-Dicarbonyl containing compounds, nitro- sation, 107 Dichloromethyl methyl ether, formylation of

porphyrins, 283 Dichloromethylpyrroles, 151 5-Dichloromethylpyrrylketones, 269 1,19-Dideoxybiladienes-ac, see bila-

dienes-ac 1,19-Dideoxybilatrienes-abc, see bila-

trienes-abc 1,19-Dideoxybilenes-b, see bilenes-b

N,N-Diethylformamide, synthesis and use, 180

Diethyl malonate, nitrosation, 107 Diethyl oximinomalonate, 104 3,4-Diethylpyrrole, synthesis, 127 Diformyldeuterohemin

pyridine hemochrome, electronic spec- trum, 302

synthesis, 302 Diformyldeuteroporphyrin dimethyl ester

electronic spectrum, 302 purification, 303 synthesis, 302

Diiminoisoindolene, 382 b-Diketones, synthesis, 129 g-Diketones, in pyrrole synthesis, 130 1,19-Dimethylbiladienes-ac

cyclization to porphyrins, 238 synthesis, 238

1,19-Dimethylbilenes-b, copper promoted

cyclization to porphyrins, 256 N,Nr-Dimethylchlorins, 353 Dimethyldeuteroporphyrin

from deuteroporphyrin, 332 dimethyl ester synthesis, 228

Dimethylformamide, solvent for porphyrin metallation, 405, 408 Dinitrogen complexes, osmium porphyrins, 465

Dioxygen complexes chromium porphyrins, 440, 443 cobalt porphyrins, 468 Griffith model, 456 hemes, 455 infrared spectroscopy, 456

iron porphyrins, 455 myoglobin, 457 Pauling model, 456 picket fence-X-ray structure, 456

superoxide formulation, 457 2,3-Diphosphoglycerate, 48 Dipropionyldeuterohemin, synthesis, 300 Dipyrroketones, see pyrrylketones 2,2-Dipyrrolylketones, see pyrrylketones 2,2'-Dipyrrolylmethanes, see dipyrryl- methanes Dipyrromethanes, see dipyrrylmethanes Dipyrrylmethanes

meso-aroyl 90 meso-chloro, 220

condensation with 5,5'-diformylpyr- rylketones, 223

conversion to bilenes-/?, 249 conversion to porphyrins, 175 conversion to pyrrylmethanes, 206 conversion to tripyrrenes, 254 couplingwith pyrromethenes, 213 detection on tic plates, 174 5,5'-dicarboxylates, decarboxylation,

179,184 differential protection of rings, 279 5,5'-diformyl, 182, 185, 187 5,5'-diunsubstituted

conversion to porphyrin, 175 coupling with pyrrylketones, 215 synthesis, 179

5-formyl, precursors of bilenes-/?, 252 5-formyl-5-unsubstituted, synthesis,

190 formylation, 180 meso-hydroxy, 220 nomenclature, 3 oxidation to pyrrylketones, 220 properties, 163-175 rearrangements, 180 synthesis

from acetoxymethylpyrroles, 169 from azafulvenium cations, 167 from bromomethylpyrroles, 169 from formaldehyde, 166 from lithium pyrrole carboxylates, 174

unsymmetric, 167

Vilsmeier-Haack formylation, 182 Dipyrrylthioketones, see Pyrrylthioketones Dry column chromatography of porphyrins, 563 Dyestuffs, phthalocyanines, 379

coprohemin-pyridine hemochrome, 319 coproporphyrin I tetramethyl ester, 319 coproporphyrin III tetramethyl ester, 319 deoxophylloerythroetioporphyrin, 493 deuterohemin, 295 deuterohemin-pyridine hemochrome, 295 deuteroporphyrin, 294 deuteroporphyrin dimethyl ester, 295 diacetyldeuterohemin-pyridine hemo-

chrome, 300

diacetyldeuteroporphyrin dimethyl ester, 300

N,N-dialkylporphyrins, 349

diazaporphyrins, 369

diformyldeuterohemin-pyridine hemochrome, 302

diformyldeuteroporphyrin dimethyl ester, 302

etioporphyrin I, 493

geoporphyrins, 493 harderoporphyrin trimethyl ester,

323

hematohemin-pyridine hemochrome, 297

hematoporphyrin dimethyl ester, 297 heme a-pyridine hemochrome, 309 hemec-pyridine hemochrome, 308 hemin chloride-pyridine hemo- chrome, 209 hyper type, 415 hypo type, 416 hypso type, 415

iron octaethylporphyrin fluoride, 414 iron octaethylporphyrin M-oxo dimer, 414 iron porphyrins, 466 iron meso -tetra(p-tolyl)-porphyrin

chloride, 415 isospirographis hemin-pyridine hemo-

chrome, 304 isospirographis porphyrin dimethyl

ester, 303 mesohemin-pyridine hemochrome, 299 mesoporphyrin dimethyl ester, 299 metalloporphyrins, see also specific

compounds, 412-417 N-methylporphyrins, 343 monoazabenzoporphyrins, 383 monoazaporphyrins, 368 nickel porphyrins, 472 normal type, 415

E

Electronic spectra N-acetylcorroles, 361 N-alkylcorroles, 358 alio type, 416

analysis and interpretation, 48 bilanes, 273 bilenes-b, 273 charge-transfer bands, 417 copper porphyrins, 472

octaethylporphyrin, 414 diprotonated, 414

osmium porphyrins, 466 oxobilanes, 273 oxorhodo type,294 pemptoporphyrin dimethyl ester, 321 photoprotoporphyrins (isomers 1 and 2) dimethyl ester, 304 phthalocyanins, 376 y-phyllohemin-pyridine hemochrome, 329

g-phylloporphyrin XV, 493 g-phylloporphyrin XV methyl ester, 329

platinum octaethylporphyrin, 414 platinum ra^Y;-tetra(/?-tolyl)-porphyrin, 415

porphyrin a dimethyl ester, 309 protoporphyrin dimethyl ester, 290 pyridine hemochromes, see specific com- pounds pyrrohemin-pyridine hemochrome, 327 pyrroporphyrin methyl ester, 327 pyrrylketones, 267, 271 rhodohemin XV-pyridine hemochrome, 328 rhodoporphyrin XV, 493 rhodoporphyrin XV dimethyl ester, 328 rhodo type, 294 ruthenium porphyrins, 466 S-411 porphyrin tetramethyl ester, 322 Spirographis hemin-pyridine hemo-

chrome, 304 Spirographis porphyrin dimethyl

ester, 303 N-substituted porphyrins, 343, 355 tetraazaporphyrins, 372 m e s o - t e t r a (p-tolyl)-porphyrin, 415

diprotonated, 415 N,N,N-trialkylporphyrins, 349

urohemin-pyridine hemochrome, 316 uroporphyrin I octamethyl ester, 316 uroporphyrin III octamethyl ester, 316 zinc octaethylporphyrin, 414

zinc meso-tetra p-tolyl-porphy rin, 415 Electrophilic substitution

bilanes, 271 pyrromethenes, 207 pyrrylketones. 268

Electrophoresis, porphyrins, 584

Enzymatic decarboxylation coproporphyrinogen III, 280 coproporphyrinogen IV, 323

Epoxyporphyrins, 246 Esterification

hematoporphyrin, 298

protohemin, 293 N-ethoxycarbonylmethylporphyrin

nmr spectra, 350 rearrangements, 351, 356 synthesis, 350, 356

X-ray structure, 346 3-Ethyl-8-acetyldeuteroporphyrin di- methyl ester, synthesis, 259 Ethyl a-oximinoacetoacetate, 102 Etioporphyrin, nomenclature, 7 Etioporphyrin I, synthesis, 211, 226 Etioporphyrin II, synthesis, 258 Etioporphyrin III

from mesohemin, 300 from mesoporphyrin, 331

Etioporphyrin IV, synthesis, 228, 259

F

Familial ferrihemoglobinemia, 31 Ferritin, 64 Fischer porphyrin synthesis, 209 Formaldehyde, incorporation into porphy- rins, 249 Formylation

copper deuteroporphyrin, 302 deuterohemin, 302 dipyrrylmethanes, 180, 182 formation of pyrrylketones, 267 pyrroles, 146

1 -Formyl- 19-methylbilenes-/?, cyclization to porphyrins, 256

Formylporphyrins, synthesis, 282 Formylpyrroles

acetals as protecting groups, 156 conversion to pyrromethenes, 199 diborane reduction, 271 Girard hydrazones as protecting groups,

156 protection, 146 synthesis, 146, 151 5-unsubstituted, 151 5-Formylpyrrylketones, 209

Formylvinyldeuteroporphyrins, 302

isomer separation by column chroma- tography, 564 isomer separation by tic, 562

2-Formyl-4-vinyl-deuteroporphyrin, see

Spirographis porphyrin a-Free pyrroles

conversion to pyrromethenes, 199, 204 reaction with acetoxymethylpyrroles, 169 reaction with bromomethylpyrroles, 169 synthesis, 162

occurrence

petroleum and bitumens, 517 sediments, 511 shales, 533 petroporphyrins distribution, 520 mass spectra, 519 structural characterization

number of isomeric porphyrins, 531 number of petroporphyrins, 528 oxidation and mass spectra, 525 oxidation to maleimides, 521 properties, 511 vanadyl porphyrins, 513, 517 Germanium porphyrins, 436 Glaucobilin, nomenclature, 18 Glyoxylic acid, reductive alkylation of pyr- roles, 124 Gold porphyrins, 471 redox chemistry, 473 synthesis, 449 Griffith model of oxygenation, 456

G

Gallium porphyrins, v-oxo dimers, 429 Gas chromatography of geoporphyrins, 488

of porphyrins, 569 Gatterman formylation, 146 Geeldikkop, 32 Gel filtration of porphyrins, 564 Geochemistry of porphyrins, 51 Geological time scale, 549 Geoporphyrins

formation, diagenetic reactions alkylation, 543 Diels-Alder adducts, 544 dimerization, 545 formation, Treibs' scheme, 505 diagnetic reactions, 505, 536 aromatization, 539 decarboxylation, 540 demethanation, 542 desterification, 538 devinylation, 541 etio series formation, 542 redox reactions, 538 fractionation, 488

gas chromatography, 488 high pressure liquid chromatography, 492

free base porphyrins, 512, 518 geological time scale, 549 identification

electronic spectra, 493 GC/MS,502 mass spectroscopy, 498 via maleimides, 503, 547

isolation, 488 kerogen porphyrins, 534 nickel porphyrins, 514, 535

H

Hafnium porphyrins, 436 Hafnium octaethylporphyrin, X-ray struc- ture, 436 Half-stercobilin, nomenclature, 20 Halogenated phthalocyanines, 376

porphyrins, 89 Hantzsch, pyrrole synthesis, 129 Harderoporphyrin, isolation, 323 Harderoporphyrin dimethyl ester, 281 Harderoporphyrin trimethyl ester, synthesis, 278

HCl number, porphyrins, 585 Hematin, 460

magnetic properties, 461 nomenclature, 25 Hematohemin, pyridine hemochrome, elec- tronic spectrum, 297 Hematoporphyrin

dehydration, 298 dimethyl ether, 297 esterification, 298 iron insertion, 298 nomenclature, 11

preparation, 297

to protoporphyrin dimethyl ester, 292 Hematoporphyrin dimethyl ester, electronic

spectrum, 297 Hematoporphyrinuria, 36 Heme, biosynthesis, 45, 65, 317 Hemetf

isolation, 310, 313 structure determination, 310 purification, 312

pyridine hemochrome, electronic spec trum, 309 Heme proteins

crevice conformation, 46

iron content, 55 resistance to denaturation, 58

Hemes carbonyl complexes, 457 dioxygen complexes, 455 ligation, 454 nitrosyl complexes, 458 nomenclature, 25 redox chemi stry, 454

Hemichrome salts, 461 infrared spectra, 461 nmr spectra, 461

Hemin iron removal, 291 isolation from blood, 291

nomenclature, 25 to protoporphyrin dimethyl ester, 291

Hemin(s),459

magnetic properties, 460 Hemin chloride, pyridine hemochrome,

electronic spectrum, 290 Hemochromatosis, 31 Hemochromogens, 55 Hemoglobin

crystallization, 55 homeostasis, 62 iron content, determination, 52 T and R states, 69

Hemoglobinometry, 52 Hemoglobinopathies, 31 Hemopexin, 60 Hemoproteinurias, 61 Hemopyrroles, synthesis, 117, 119, 127 Heptacarboxylic acid porphyrins, Type III,

synthesis, 280 Hexacarboxylic acid porphyrins, Type III,

synthesis, 2 80 Hexapyrrenes, 251

High pressure liquid chromatography of porphyrins, 492, 558, 574

Histohematins, 30 History

metalloporphyrins, 393 of porphyrin and derivatives, 29-99

Homeostasis, hemoglobin, 62 Homoazaporphyrins, nomenclature, 21 Homoporphyrins, 351, 356 Hydrides, rhodium porphyrins, 471 Hydrobilins, nomenclature, 16 Hydrodic acid

deiodination of iodopyrroles, 124 H3PO2, reductive alkylation, 124

Hydropyrrins, nomenclature, 17 1- Hydroxy-2-desvinyl-2-formylethylidene-

protoporphyrin, see Photoprotoporphy- rin i somer 2

3-Hydroxy-4-desvinyl-4-formylethylidene- protoporphyrin, see Photoprotoporphyrin isomer 1

meso Hydroxdipyrromethanes 220 2- Hydroxymethylpyrrole, porphyrin pre-

cursor, 86 Hyperelectronic spectra, 415 Hypo electronic spectra, 416 Hypophosphorous acid, reductive alkyla-

tion of pyrroles, 124

I

Imidines, intermediates in phthalocyanine synthesis, 380

Indium porphyrins, 429 Infrared spectra characteristic vibrations of metal-axial

Iigand chromophores, 422 hemichrome salts, 401 iron porphyrins, 450

carbonyl complexes, 457, 466 metalloporphyrins, 422 molybdenum porphyrins, 445 pyrrylketones, 267 rhenium porphyrins, 445 tungsten porphyrins, 445 Inositol hexaphosphate, 48 Iodination, of pyrroles, 162 Iodinative decarboxylation, pyrrole car- boxylic acids, 124

Iodopyrroles deiodination, 163 synthesis, 162 Ionic radius effect on oxidation states of metallopor- phyrins, 411 of metal, effect on porphyrin metallation, 411

Iridium porphyrins, synthesis, 449 Iron sorption, 64

in heme and heme proteins, 55 insertion into hematoporphyrin, 298 migration in body, 63 removal from hemin, 291 raeso-tetraphenylporphyrin-M-oxo dimer

X-ray structure, 400 transfer into cells, 64

Iron octaethylporphyrin fluoride, electronic spectrum, 414

Iron octaethylporphyrin /u-oxo dimer, electronic spectrum, 414 Iron porphyrins, see also Hemes, Hemo- chromes, Hemins, Hematins, Hemi- chrome salts and specific compounds

carbonyl complexes, 457 infrared spectra, 457, 466

cis and trans effects, 465 dioxygen complexes, 455 electronic spectra, 466

infrared spectra, 450 ligand exchange, 448 magnetic properties, 450 metal alkyls, 470 nitrido complexes, 462

nitrosyl complexes, 458 nomenclature, 25

picket fence porphyrins, 455 redox chemistry, 448, 462

synthesis, 448 Iron protoporphyrin chloride, X-ray struc- ture, 396

Iron meso tetra-p-tolyporphyrin chlo ride,- electronic spectrum, 415

Isocoproporphyrin tetramethyl ester, syn- thesis, 278,280

Isoharderoporphyrin dimethyl ester, syn- thesis, 281

Isoharderoporphyrin trimethyl ester, syn- thesis, 278 Isolation of natural porphyrins, 289

Isopemptoporphyrin dimethyl ester, synthe- sis, 244, 257, 275, 281 Isoporphyrin, nomenclature, 9 Isopurpurin 5, nomenclature, 8 Isorhodinporphyring5, nomenclature, 7 Isospirographis hemin, electronic spectrum, 304 Isospirographis porphyrin

electronic spectrum, 303 from photoprotoporphyrin, 305 pyridine hemochrome, electronic spec- trum, 304

Isotopically labelled porphyrins, 244, 248, 284,285

K

Kerogen porphyrins, geochemical, 534 Keto esters, nitrosation, 107 Kinetics of porphyrin metallation, 409 Knorr synthesis of pyrroles, 102-128

execution, 107 Johnson variation, 104 Kleinspehn variation, 104

Knorr's pyrrole, 104

L

Lanthanide porphyrins, 428, 432 Lead porphyrins, 436 Lead tetraacetate

oxidation of dipyrrylmethanes to pyrryl- ketones, 220

oxidation of methylpyrroles, 149 Ligands

cobalt porphyrins, 452, 468 exchange, metalloporphyrins during

chromatography, 420 hemes, 454 identification, metalloporphyrins, 421 iron porphyrins, 448 nickel porphyrins, 472 osmium porphyrins, 452 rhodium porphyrins, 452

Lithium nitrite, nitrosating agent, 107 Lithium porphyrins, 424

M

MacDonald porphyrin synthesis, 177 Magnesium, insertion into porphyrins, 427 Magnesium alkoxides, magnesium insertion, 409

Magnesiumchlorinp6, preparation, 325 Magnesium 3,5-di-/-butyl-4-hydroxy- toluene, magnesium insertion, 427 Magnesium octaethylporphyrin, photo- oxidation, 417 Magnesium porphyrins, 425

role in photosynthetic pigments, 427 synthesis, 427

Magnetic properties hematins, 461 hemins, 460 iron porphyrins, 450

Maleimides

from azaporphyrins, 342 from geoporphyrins, 503, 547 from petroporphyrins, 528

Manganese porphyrins manganoglobin, 443 f i-oxo dimer, 444 reaction with dioxygen, 443 kkrole,, in photosynthesis, 443 synthesis, 442

Manganoglobin, 443 Mannich bases, pyrrolic, porphyrin precur sors , 87 Mass spectra

N-alkylcorroles, 360 N,N-dialkylcorroles, 360

N,N-dialkylporphyrins, 349, 355 geoporphyrins, 498

metalloporphyrins, 422 petroporphyrins, 519 phthalocyanines, 378 N,N,N-trialkylporphyrins, 348, 354

Meconium, isolation of porphyrins, 322 Mercury porphyrins, 426

synthesis, 427 Mesobilirhodins, nomenclature, 20 Mesobilirubin, nomenclature, 18 Mesobilirubinogen, nomenclature, 18 Mesobiliverdin, nomenclature, 18 Mesohemin

conversion to etioporphyrin III, 300 preparation, 299 purification, 564

pyridine hemochrome, electronic spec trum,- 299 Mesoporphyrin

conversion to etioporphyrin III, 331 conversion to 1,3,5,8-tetramethyl- 2,4-dimethyl-6,7-dipropylporphyrin, 333

nomenclature, 7 Mesoporphyrin dimethyl ester electronic spectrum, 299 synthesis, 242, 257, 260, 261, 269, 274, 275, 277, 299

Mesoporphyrin II dimethyl ester, synthesis, 226 Mesoporphyrin III dimethyl ester, synthe-

sis, 240 Mesoporphyrin XI, synthesis, 275, 278 Mesoporphyrin XI dimethyl ester, synthe- sis, 257 Mesoporphyrin XIII dimethyl ester, synthe-

sis, 228 Mesotetraphenylporphyrin see also Metaloporphyrins chromatography, 571 synthesis, 89 Metal alkoxides, for porphyrin metallation, 49 Metal alkyl

cobalt porphyrins, 470 iron porphyrins, 470

for porphyrin metallations, 408 Metal carbonates, see Porphyrin chromatog- raphy, 567 Metal carbonyls, for porphyrin metallation,

409 Metallation of porphyrins, 390, see also

Metalloporphyrins MetalIo /V-substituted porphyrins, 342 Metallodiazaporphyrins, 369 Metallophthalocyanines, 377

heats of sublimation, 587 synthesis, 374, 377 Metalloporphyrins, 389-483, see also specific compounds and Porphyrin, metallo

acid lability, 418 alkali metals, 424 alkaline earth metals, 425 alio complexes, 416 axial ligand identification, 421 charge transfer bands, 417 chromatography, 419, 553-580

choice of method, 554 column, 564 high pressure liquid, 558, 574 Iigand exchange, 420 paper, 561, 565

precautions, 557 thin layer, 563

classification, 395 coordination types, 396 demetallation by acids, 417 electronic spectra, 412-417, see also

Electronic spec tra, and sp ecific compounds

esters, paper chromatography, 565 thin layer chromatography, 567 hyper, 415 hypo,415 normal, 415 group(s) la, 424

IIa and lib, 425

IIIaand IIIb, 428 IVa, IVb, Va, and Vb, 432

Via and Via, 440 VIIIa and lb, 447-474

heats of sublimation, 587 historical aspects, 393 infrared spectroscopy, 422 lanthanides, 428

Ligand exchange during chromatography, 420

mass spectroscopy, 422 Mossbauer spectroscopy, 423 naturally occurring, 393 oxidation states, 412 periodic table of, 394 purification, 419 Raman spectroscopy, 423 stability, 417 stability index, 418 stability TPPvsOEP, 419 stable oxidation states, 411 synthesis

acetic acid as solvent, 405 benzonitrile as solvent, 405, 407

DMFas solvent, 405, 408

effect of ionic radius, 411 effect of oxidation state of metal, 410 kinetics, 409

metal acac, 405, 407

metal alkoxides, 405, 408

metal carbonyls, 408, 409 metal complexes, 405 phenol as solvent, 408, 409 pyridine as solvent, 405, 407 tetramethylureaas solvent, 408 zinc complexes, 425 Metallotetraazaporphyrins, 371 Metallotriazabenzoporphyrins, 386 b-Methoxypyrroles, 134 1-Methyl-19-alkyltetradehydrocorrins conversion to meso-alkylporphyrins, 247

synthesis, 247 1- Methyl-19-bromobiladienes-flc

cyclization to por phyrins, 242 synthesis, 242

Methyl 4-(2-methoxycarbonylethyl)-3- methoxycarbonylmethyl-5-methylpyr- role-2-carboxylate, synthesis, 111

2- Methyl-3-oxobutyraldehyde, 105 5-Methyl-5'-unsubstituted pyrromethenes, conversion to biladienes-^c, 242 l-Methylbiladienes-ac, cyclization to por phyrins,- specific examples and experi- mental details, 258 I-Methylbilenes-/? copper promoted cyclization to porphy- rins, 256 cyclization to porphyrins, specific exam- ples and experimental details, 259 N-Methylchlorins

nmr spectra, 353 synthesis. 352 /V-MethylcoiTole, X-ray structure, 358 Methylene bridged porphyrins (N-Co), 350 N-Methyletioporphyrins, 381 N-Methylporphyrins, electronic spectra, 343 meso-Methylporphyrins, synthesis, 242 Methylpyrroles

acetoxylation, 149 conversion to aldehydes, 150 conversion tocarboxylic acid, 156, 159 conversion to pyrromethenes, 204 conversion to trichloromethylpyrrole, 160 halogenation, 148, 150, 156

1-Methyltetradehydrocorrins, from biladienes ac, 246

Miranda family, 33 Modification of natural porphyrins, 289 Molybdenum porphyrins

infrared spectra, 445 Niobium meso-tetraphenylporphyrin synthesis, 441 (Nb2O3 TPP), X-ray structure, 400

Niobium meso-tetraphenylporphyrin oxo X-ray structures, 444 Molybdenum meso-tetraphenyIporphyrin dioxo complex, X-ray structure, 398 Monoazabenzoporphyrins

complex, X-ray structure, 398 M-Nitrido iron porphyrins, 462 Nitrosation, /3-dicarbonyl containing com- pounds, 107 Nitrosyl complexes hemes, 458 iron porphyrins, 458 Nmr spectra N-acetylcorroles, 361 N-alkylcorroles, 357 N,N-dialkylcorroles, 359 N,N-dialkylporphyrins, 348, 354 N-ethoxycarbonylmethylporphyrin, 350 N,N-bis ethoxycarbonylmethylporphyrin, 350

electronic spectra, 386 synthesis, 383

Monoazaporphyrins, 365-368 basicity, 367 from biladienes-tfc, 366 electronic spectra, 368 reduction, 367 synthesis, 365

from verdohemins, 366 Monobenztetraazaporphyrins, 380 Monographs, in porphyrin field, 38 Monohydroxyethyldeuterohemin resorcinyl ether, 296 hemichrome salts, 461

N-methylchlorins, 353 N-methylporphyrins, 344 Nomenclature, 1-27

Monohydroxyethyl monovinyldeuteropor- phyrin, 292 Mbssbauer spectroscopy, metalloporphy-

rins, 423 Myoglobin crystallization, 56 oxygenation, 457 Myohematins, 30

annelated systems with fused rings, 10 lineartri- and tetrapyrroles, 14-19 metal complexes, 21-25

IUPAC rules, 23 trivial names, 24

porphyrins, 4-14 parent systems, 4, 9 trivial nomenclature, 6, 10

N type nomenclature, 5, 10 pyrroles, 2

ring contracted and ring expanded sys- tems, 19 semisystematic nomenclature, 11 systems with two pyrrole rings, 3 b-Norbiladienes-ac, 241

Naturally occurring metalloporphyrins, 393

Naturally occurring porphyrins, isolation and modification, 289

Neoporphyrin, 4 nomenclature, 10 Neopurpurins, nomenclature, 8 Nickel octaethylporphyrin. X-ray struc- ture, 396 Nickel porphyrins

O

Octaalkylporphyrins, chromatography crystalline, naturally occurring, 535 column, 570 electronic spectra, 472 paper, 570 geochemical, 514, 535 tic, 570

Octaethylporphyrin ligand exchange, 472 redox chemistry, 473 diprotonated electronic spectrum, 414

synthesis, 449 Niobium octaethylporphyrin, X-ray struc- ture, 436 Niobium porphyrins, 435

electronic spectrum, 414 HI3 adduct, X-ray structure, 401 metal complexes compared to me so-tetm-

phenylporphyrin, 395

P synthesis, 88 Octamethylporphyrin, synthesis, 87 Ooporphyrin, 33 Oorhodein, 33

Paal-Knorr, pyrrole synthesis, 129 Palladium octaethylchlorin, 407 Pauling model of oxygenation, 456 Pemptoporphyrin

Orientation reversal sequence, synthesis of formylpyrroles, 156

Osmium porphyrins isolation, 321 carbonyl complexes, 463, 466 nomenclature, 11 cis and trans effects, 465 synthesis, 244, 252

Pemptoporphyrin dimethyl ester, synthesis, 278,281

dinitrogen complexes, 465

dioxocomplexes, 464 electronic spectra, 466 Pentacarboxylic acid porphyrins Type III, ligand exchange, 452 synthesis, 280

2,4-Pentanedione, Michael addition to acry- redox chemistry, 452, 464 synthesis, 449

Oxidation, see also Redox Iate, 126

Periodic table of metalloporphyrins, 394 Peroxytitanium octaethylporphyrin, 435 Petroleum, porphyrin occurrence, 517 Petroporphyrins, see Geoporphyrins Phenol, solvent for porphyrin metallation, 405, 407

metalloporphyrins, 412 of metals, effect on porphyrin metallation,

410 porphyrinogens, 94 stable, metalloporphyrins, 411 using eerie ammonium nitrate, 220 lead tetraacetate, 149, 220 sulfuryl chloride, 148, 150, 159, 220 t-butyl hypochlorite, 148, 150, 159, 255, 269

Pheophorbides, nomenclature, 8, 13 Pheophorbide a, 326 Pheophytin(s), nomenclature, 13, 14 Pheophytina, 326 Pheoporphyrins, nomenclature, 8 Pheoporphyrin a5, from Rhodoporphyrin, 332

2,3-Oxidoporphyrins, 247 Oximes, reduction, 108 Oxobilanes a-oxobilanes, 255

Phlorin, nomenclature, 13 Phorbin, nomenclature, 4 Phosphorus porphyrins, 436 Photooxidation

cyclization to porphyrins, 269 reduction, 271 synthesis, 270 magnesium octaethylporphyrin, 417

Photoprotoporphyrins b-oxobilanes conversion to isospirographis porphyrin,

305 conversion to oxophlorins, 276 cyclization to porphyrins, 274 synthesis, 274 electronic spectra, 273 Oxo complexes, osmium porphyrins, 464 m-Oxo dimers aluminum, 429 gallium, 429 manganese, 444 scandium, 431 Oxophlorins acetylation, 277 from &-oxobilanes, 276 reduction, 277 Oxorhodo-type electronic spectra, 294 a-Oxymesoporphyrin, 284 b-Oxymesoporphyrin, 284 Oxyporphyrins, see Oxophlorins

conversion to Spirographis porphyrin, 305

electronic spectra, 304 from protoporphyrin, 293 separation by chromatography, 305 synthesis, 306

Photosynthesis, magnesium, role, 427, 443 Phthalocyanines, 374-380

analogs, 380-383 p-anion radicals, 377 dyestuffs, 379

electronic spectra, 376 halogenation, 376

heats of sublimation, 587 imidines, intermediates in synthesis, 380 mass spectra, 378

mechanism of formation, 375 metal complexes, 374, 377 metal derivatives, 377 oxidation, 376 sulfonated, 376 synthesis, 374

Porphomethene intermediates in porphyrin synthesis, 98 nomenclature, 13

Porphyrazines, see Tetraazaporphyrins Porphyria, 31 drug induced,36 Porphyrin(s), see also geo-, metallo- and specific compounds

uranium, X-ray structure, 399 X-ray structure, 376

Phycobiliverdin, nomenclature, 19 Phycobiliviolin, nomenclature, 19 Phycocyanin, nomenclature, 19 Phycocyanobilin, nomenclature, 19 Phycoerythrobilin, nomenclature, 19 Phyllochlorin, preparation, 327 Phylloerythrin

meso-alkyl, 242, 247 aza,365,388 bearing labile groups, synthesis, 280 biological markers, 486 bromo, hydrogenolysis, 282 capped,455 chromatography, 553-580 countercurrent distribution, 584 crystallization, 585 electrophoresis, 584 epoxy,246

nomenclature, 11 preparation, 327

Phylloporphyrin nomenclature, 11

preparation, 327 g-Phylloporphyrin, nomenclature, 7 g-Phylloporphyrin IV methyl ester, synthe- sis, 261

esters, chromatography, 565 esterification, 576 vV-ethoxycarbonyl, 350 X-ray structure, 345 a and b faces, nomenclature, 22 Fischer synthesis, 209 b-formylation, 282 from azafulvenium ions, 93 from biladienes-flc, 248, 258, 261 from bilenes-6, 249, 259, 260 from chlorophylls, 324-329 from 5,5'-diformylpyrrylketones and

g-Phylloporphyrin XV, preparation, 329 g-Phylloporphyrin XV methyl ester, synthe- sis, 239, 242,261 Phytoporphyrin, nomenclature, 11 Picket fence porphyrins, 455 Piloty-Robinson, pyrrole synthesis, 132 Platinum octaethylporphyrin, electronic

spectrum, 414

Platinum meso-tetra(p-toly l)porphyrin, dipyrrylmethanes, 221 from 1,19-dimethylbilenes-b and copper, electronic spectrum, 415

Platinum porphyrins, 471 256 from dipyrrylmethanes, 175, 209 redox chemistry, 472 from l-formyl-19-methylbilenes-6, 256 synthesis, 449

Polyamide column chromatography of metalloporphyrins, 564

from Mannich bases, 87 from meconium, 322

from 1-methylbilenes-b and copper, 256 tic of metalloporphyrins, 563 Polymers, silicon phthalocyanines, 402 Polypyrromethenes, intermediates in por- phyrin synthesis, 95 Porphin

from monopyrroles, 85-100 from a-oxobilanes, 269, 275 from b-oxobilanes, 274, 278 from porphodimethenes, 98 from porphomethenes, 98 nomenclature, 4 from porphyrinogens, 91 synthesis, 85

Porphinato, nomenclature, 23 Porphobilinogen

from pyrroles, 85-100 from pyrromethenes, 211

and copper, 239 gas chromatography, 569 gel filtration, 564 geochemistry, 51, 485-551 halogenated, 89

from 6-azaindoles, 135 lactam, synthesis, 135

Porphodimethene(s) intermediates in porphyrin synthesis, 98

nomenclature, 13

HCl-number, 585 conversion to coporporphyrin III, 329 isotopically labelled, 244, 248 nomenclature, 7

heats of sublimination, 587 isotopically labeled, 244, 248, 284 MacDonald synthesis, 177 oxidation to diformyldeuteroporphyrin,

302 metabolism, regulation, 37 metal insertion, see metalloporphyrins reduction, 299

Protoporphyrin dimethyl ester meso-methyl, 242 purification, 581-589 chromatography, 292

electronic spectrum, 290 purity, criteria, 582 formation of photoprotoporphyrin, 293 meso-pyrryl, 240 from hematoporphyrin, 292 regulation of metabolism, 37 from hemin, 291 related to Chlorobium chlorophylls, 257 light sensitivity, 293 S-411,278 reduction, 299 sublimination, 586

synthesis, 244, 248, 257, 278 Protoporphyrin I dimethyl ester, synthesis, 278,281

N-substituted, see N-substituted porphy rins and specific compounds 2+2 synthesis, 224-230 synthesis, see Synthesis and specific compounds mechanistic considerations, 90 substituent effects, 96 meso-tetramethyl, 90 meso-tetraphenyl, 89 vinyl containing, synthesis, 244, 281 water soluble, 573 Porphyrins, purification, 312 Porphyrins dimethyl ester, electronic spec- trum, 309 Porphyrinc preparation, 309

Protoporphyrin IX, see Protoporphyrin Protoporphyrin di-tert-butyl ester, 306 Pterobilin, nomenclature, 20 Purification

hemins, 564

metalloporphyrins, 419 porphyrins, 581-589

Purpurin 5, nomenclature, 7 Purpurin 7

nomenclature, 7 preparation, 327

Purpurin 9, 7 Pyridine, solvent for porphyrin metallation,

405 pyridine hemochrome, electronic spec- trum, 308 Pyrrocolls, 161

Pyrroketones, see Pyrrylketones 2-(2H-pyrrol-2-ylidenemethyl)-pyrrole,

Porphyrinc tetramethyl ester, electronic spectrum, 308

Porphyrin S-411, isolation, 322 Porphyrinogens meso-acetoxy, 277

see Pyrromethenes Pyrroleacetic acids, from reductive alkylation

of pyrroles, 124 Pyrrole(s) a-acetoxymethyl, 149 from ammonium mucate, 129 azafulvenium ions, 93 from azines, 132 t-butyl ester cleavage, 124 containing, 117 from N-carbethoxyglycine esters, 134 carboxylates, 124

intermediates in porphyrin synthesis, 91 nomenclature, 4, 13 oxidation, 94

N,N,N,N-tetramethyl, 349 Potassium porphyrins, 424 Protohemin

conversion to deuterohemin, 295 esterification, 293 purification, 564

reaction with diazomethane, 213 decarboxylation, 143

a-carboxylates, 154, 156, 159 a-chloromethyl, 148 crypto, 104, 117

reduction, 299 Protopheophytins, nomenclature, 13 Protoporphyrin

chromatography, 293

cyanovinyl, 147 dehalogenation, 124, 154 a-dichloromethyl, 151 3,4-diethyl, synthesis, 127 from g-diketones, 130 esters, hydrolysis, 143, 153

Pyrroporphyrin methy l ester , sy nthesis, 24 2 Pyrroporphyrin XV methyl ester

preparation, 327 synthesis, 262

Pyrrylcarbinyl cations, see Azaful- venium ions

Pyrrylketones transbenzylation, 125 formyl, acetals, 156 5,5'-bisacetoxymethyl, 216

hydrazones, 156 5,5'-bischloromethyl, 216 to pyrromethenes, 199 5-chloromethyl, 269 synthesis, 146, 151

a-free, synthesis, 162 cleavage by bromine, 217 coupling with dipyrrylmethanes, 215

to dipyrrylmethanes, 169 diborane reduction, 271 to pyrromethenes, 199, 204

hemo-synthesis, 117, 119, 127 a-hydroxymethyl, 86 iodo,162 Knorr's, 104 b-methoxy, 134 a-methyl, 148

5-dichloromethyl, 269 5,5'-diformyl, 216, 221

condensation with dipyrrylmethanes, 223

5,5'-dimethyl, oxidation to diformyl, 221 from dipyrrylmethanes, 220 electronic spectra, 267, 271 electrophilic substitution, 268 5-formyl, 269 ir spectra, 267

to pyrromethenes, 2 04 reductive al kylation, 124 saponification, 143

synthesis from acyclic precursors, 101 fromp-toluene sulfonyl glycine esters, 134 a-trichloromethyl, 160 b-vinyl-containing; precursor synthesis, 121

5-methyl, oxidation with/-butylhypo- chlorite, 269

nomenclature, 3 properties, 267

reduction to dipyrrylmethanes, 220, 268 synthesis, 217, 220, 266 thio, 218

Pyrrole carboxylic acids, decarboxyla- tion, 124, 144 Pyrroloindolizenes, from 3-acetyldipyr- unsymmetric, 218

meso-Pyrrylporphyrins, synthesis, 240 Pyrrylthioketones, 218

rylmethanes, 251 meso-Pyrrolylporphyrins, 252 Pyrromethanes, see Dipyrrylmethanes Pyrromethenes

R

bromination, 207 Raman spectroscopy, metalloporphyrins,

423 meso-chloro, 220

cis- and rra/w-isomers, 95 Rearrangements

7V-alkylcorroles, 358 dipyrrylmethanes, 180 A-ethoxycarbonylmethylporphyrin, 351, 356

copper catalyzed dimerization coupling with dipyrrylmethanes, 213 5,5'-dibromo-porphyrin synthesis, 211 5,5'-dimethyl-porphyrin synthesis, 211

from dipyrrylmethanes, 206 Reconstitution, apo myoglobin-Ytterbium electrophilic attack, 207 mesoporphyrin, 431 Redox chemistry, see also oxidation and re- duction cobalt porphyrins, 452 copper porphyrins, 473 gold porphyrins, 473 hemes, 454

from a-free pyrroles, 199, 204 a-methyl, oxidation, 206 nomenclature, 3 perbromides, 205 properties, 198 synthesis, 198-207

Pyrroporphyrin, nomenclature, 6, 7, 11

iron porphyrins, 448, 462 Rhodoporphyrin IV diethyl ester, synthesis 261 nickel porphyrins, 473

osmium porphyrins, 452, 464 Rhodoporphyrin V diethyl ester, synthesis, 261 platinum porphyrins, 472

rhodium porphyrins, 452, 471 Rhodoporphyrin XII diethyl ester, synthe- sis, 261 ruthenium porphyrins, 448, 464

silver porphyrins, 473 Rhodoporphyrin XV, preparation, 328 Rhodoporphyrin XV diethyl ester, synthe sis, 235, 242, 261 Rhodoporphyrin XV dimethyl ester, synthesis, 278

zinc porphyrins, 427 Reduction, see also Redox chemistry

bromoporphyrins, 282 catalytic, iodopyrroles, 124 diborane, 127 Rhodo type electronic spectra, 294

Rothemund porphyrin synthesis, 86, 88 monazaporphyrins, 367 oximes, 108 mechanism, 90

Rubidium porphyrins, 424 Ruthenium porphyrins

a-oxobilanes, 271 oxophlorins, 277 protohemin, 299 carbonyl complexes, 463, 466 protoporphyrin, 299 cis and trans effects, 465 pyrrylketones, 267

to dipyrrylmethanes, 220 electronic spectra, 466 redox chemistry, 448, 464

tetraazaporphyrins, 372 synthesis, 448 xanthoporphyrinogens, 277

Reductive alkylation, pyrroles, 124 Regulation of porphyrin metabolism, 37 Reviews, in porphyrin field, 38 Rhenium porphyrins

S

S-411 porphyrin trimethyl ester, synthesis, 278 infrared spectra, 445

synthesis, 442, 446 Sapphyrin, nomenclature, 21 Scandium porphyrins, 431 X-ray structure, 447

bis-(Rhenium tricarbonyl)meso-tetraphe- m-oxo dimers, 431 Sediments, porphyrin occurrence, 511 Sephadex (LH-20) porphyrin chromatog- raphy, 568 Shales, porphyrin occurrence, 533 Sideropenia, 31

nylporphyrin, X-ray structure, 399 Rhodin g3, nomenclature, 7 Rhodin g5 nomenclature, 7 Rhodin g7, nomenclature, 7

preparation, 326 Rhodinporphyrin g5, nomenclature, 7 bis-(Rhodium dicarbonyl)octaethylpor-

Silica-gel tic of porphyrins, 562 Silicates, porphyrin chromatography, 567 Silicon phthalocyanine, polymers, 402 Silicon porphyrins, 436

phyrin, X-ray structure, 399 Rhodium N-methyloctaethylporphyrin, 346 Rhodium porphyrins silylated,503

Silver porphyrins carbonyl complexes, 471

hydrides, 471 redox chemistry, 473 ligand exchange, 452 synthesis, 453

Sodium porphyrins, 424 Soret region, 48, 414 Spirographis hemin

metal alkyls, 470 redox chemistry, 452, 471 synthesis, 448, 470

Rhodochlorin, preparation, 327 Rhodoporphyrin

crystallization, 55 electronic spectrum, 304

Spirographis porphyrin conversion to pheoporphyrin g5, 332

nomenclature, 6, 7 Rhodoporphyrin I diethyl ester, synthesis, 261

isolation, 304 nomenclature, 12 from photoprotoporphyrin, 305

pyridine hemochrome, electronic spec- trum, 304

bilenes-b, 249, 255 bismuth porphyrins, 439 boron porphyrins, 429 cadmium porphyrins, 426 calcium porphyrins, 426 chlorohemin, 33 chromium porphyrins, 440 cobalt porphyrins, 449, 468 copper etioporphyrin I, 239 copper etioporphyrin II, 240 copper porphyrins, 449 coproporphyrin 1,211 coproporphyrin II, 240 coproporphyrin II tetramethyl ester, 226, 258

separation from isospirographis porphy- rin, 305

synthesis, 244, 305 Spirographis porphyrin dimethyl ester

electronic spectrum, 303 synthesis, 281

Stability, metalloporphyrins, 419 Stability index, metalloporphyrins, 418 Stercobilin, nomenclature, 18 Stercobilinogens, nomenclature, 20 Strontium porphyrins, 426 Sublimination

heats of, 587 coproporphyrin III, 228 porphyrins, 586

b-Substituted porphyrins, from monopyr- roles, 87

coproporphyrin III tetramethyl ester, 248, 257, 260, 274, 275,277

coproporphyrin IV tetramethyl ester, 257, N-Substituted porphyrins, 341-357 250, 275

cytodeuteroporphyrin, 240, 310 deoxyphylloerythroetioporphyrin, 252,

basicity, 344 demethylation, 343 electronic spectra, 343, 355

256, 262 metal complexes, 342 deuteroporphyrin dimethyl ester, 243, 262 diacetyldeuteroporphyrin, 240, 201 diacetyldeuteroporphyrin dimethyl

nmr spectra, 344, 354 synthesis, 347, 351, 354 X-ray structure, 363

Sulfolane, for porphyrin metallation, 408 Sulfuryl chloride

ester, 226, 250, 259 N,N-dialkylcorroles, 359 N,N-dialkylporphyrins, 346, 352, 354 diazabenzoporphyrins, 383 diazaporphyrins, 369 3,4-diethylpyrrole, 127 diformyldeuteroporphyrin, 302 5,5'-diformylpyrrylketones, 221 b-diketones, 129 1,19-dimethylbiladienes-flc, 238 dimethyldeuteroporphyrin dimethyl

conversion of dipyrrylmethanes to pyrrylketones, 207

methylpyrrole chlorinations, 148, 150, 159 oxidation of dipyrrylmethanes to pyrrylketones, 220 Symposia

in porphyrin field, 40 Synthesis

N-acetylcorroles, 361 ester, 228

dipropionyldeuterohemin, 300 dipyrrylmethanes, 166 N-ethoxycarbonylmethylporphyrin, 350,

4-acetyldeuteroporphyrin diethyl ester, 259

3-acetyl-8-ethyldeuteroporphyrin dimethyl ester, 259

356 alkali metal porphyrins, 424 N,N-bis-ethoxycarbonylmethylporphyrin,

350 alkaline earth porphyrins, 425

N-alkylcorroles, 357 3-ethyl-8-acetyldeuteroporphyrin aluminum porphyrins, 429

dimethyl ester, 259 etioporphyrin I, 211, 226 etioporphyrin II, 258 etioporphyrin III, 300 etioporphyrin IV, 228, 259 formylporphyrins, 282 germanium porphyrins, 436

antimony porphyrins, 436, 439 arsenic porphyrins, 436, 439 azaporphyrins, 365-384 barium porphyrins, 426 beryllium porphyrins, 425 biladienes-ac, 238, 242, 248 bilatrienes-abc, 246

gold porphyrins, 449 hafnium porphyrins, 436 harderoporphyrin dimethyl ester, 281 harderoporphyrin trimethyl ester, 278 hematoporphyrin, 297 hemopyrroles, 127

phosphorus porphyrins, 436 photoprotoporphyrins, 306 phthalocyanines, 374 g-phylloporphyrin IV methyl ester, 261 g-phylloporphyrin XV methyl ester, 239,

242, 261 platinum porphyrins, 471 porphyrin c, 309 potassium porphyrins, 424 protoporphyrin dimethyl ester, 244, 248,

hexacarboxylic acid porphyrins, type III, 280

indium porphyrins, 429 iodopyrroles, 162 iridium porphyrins, 449, 470 iron porphyrins, 448 isocoproporphyrin tetramethyl ester, 278,280

257,278,291 protoporphyrin 1 dimethyl ester, 278, 281 pyrrole(s), 101-128 pyrromethenes, 198-207 pyrroporphyrin XV methyl ester, 242, 262 pyrrylketones, 216, 266 meso-pyrrylporphyrins, 240 rhenium porphyrins, 442, 446 rhodium porphyrins, 448, 470 rhodoporphyrin I diethyl ester, 261 rhodoporphyrin IV diethyl ester, 261 rhodoporphyrin V diethyl ester, 261 rhodoporphyrin XII diethyl ester, 261 rhodoporphyrin XV diethyl ester, 235,

isoharderoporphyrin trimethyl ester, 278, 281

isopemptoporphyrin dimethyl ester, 244, 257,275,281

isospirographis porphyrin, 305 lanthanide porphyrins, 428, 432 lead porphyrins, 436 lithium porphyrins, 424 magnesium porphyrins, 427 manganese porphyrins, 442 mercury porphyrins, 427 mesohemin, 299

242,261 rhodoporphyrin XV dimethyl ester, 278 rubidium porphyrin, 424 ruthenium porphyrins, 448 S-411 porphyrin, 278 scandium porphyrins, 431 silicon porphyrins, 436 silver porphyrins, 453 sodium porphyrins, 424 Spirographis porphyrin, 244, 304 Spirographs porphyrin dimethyl ester, 281

mesoporphyrin dimethyl ester, 226, 242, 257, 260, 261, 269, 274, 275, 277, 299 mesoporphyrin III dimethyl ester, 240 mesoporphyrin XI, 275, 278 mesoporphyrin XI dimethyl ester, 257 mesoporphyrin XIII dimethyl ester, 228 metallophthalocyanines, 374, 377 1 -methyl- 19-alkyltetradehydrocorrins, 247

1-methyl-19-bromobiladienes-ac, 242 N-methylchlorins, 352 meso-methylporphyiins, 242 1-methyltetradehydrocorrins, 246 molybdenum porphyrin, 441 monazaporphyrins, 365 nickel porphyrins, 449 niobium porphyrins, 436 octaethylporphyrin, 88 octamethylporphyrin, 87 osmium porphyrins, 449 a-oxobilanes, 270 b-oxobilanes, 274 pemptoporphyrin, 244, 252 pemptoporphyrin dimethyl ester, 278, 281 pentacarboxylic acid porphyrins, 280

strontium porphyrins, 426 N-substituted porphyrins, 347, 351, 354 tantalum porphyrins, 436 technetium porphyrins, 442, 446 tetraazaporphyrins, 370, 373 rapso-tetraphenylporphyrins, 89 thallium porphyrins, 429 thorium porphyrins, 436 tin porphyrins, 436, 439 titanium porphyrins, 435 N,N,N-triaikyIporphyrins, 347, 354 triazabenzoporphyrins, 384 tungsten porphyrins, 441 vanadium porphyrins, 435 vinylporphyrins, 244, 281

Tin octaethylporphyrin, X-ray struc- ture, 437 Tin porphyrins, 436, 439 Tin meso tetraphenylporphyrin dichloide,

yttrium porphyrins, 431, 437 zinc porphyrins, 427 zirconium porphyrins, 436

X-ray structure, 397 Titanium octaethylporphyrin, peroxy com- plex, 435 Titanium porphyrins, 435 Titanium meso tetraphenylporphyrin oxo

T

Talc, metalloporphyrin chromatography, 569

Tantalum porphyrins, 436 Technitium porphyrins

complex, X-ray structure, 397 p-Toluenesulfonyl glycine esters, pyrrole

synthesis, 442, 446 precursors, 134 Transbenzylation, of pyrrole carboxylate es ters, 125 Trans effect, 465 Transferrin, 64 N N ,N-Trialkylporphyrins electronic spectra, 349 mass spectra, 349, 355 nmr spectra, 348, 354 synthesis, 347, 354 3,4,5-Trialkylpyrroles, 143 Triazabenzoporphyrins metal complexes, 386 synthesis, 384 Tribenztetraazaporphyrins, 380 Trichloromethylpyrroles hydrolysis, 161 synthesis, 160 N,N,N-Trimethylchlorins, 353 Trimethyloxonium tetrafluoroborate,

X-ray structures, 447 meso-Tetraarylporphyrins

unsymmetrically substituted, 89 synthesis, 89

Tetraazabenzoporphyrins, see Phthalo- cyanines

Tetraazaporphyrins, 370-373 electronic spectra, 372 metal complexes, 371 reduction, 372

synthesis, 370, 373 Tetrabenzoporphyrins, nomenclature, 1 0

l,3,5,8-Tetramethyl-2,4-diethyl-6,7- dipropylporphyrin, from mesoporphyrin, 333

w^so-Tetramethylporphyrin, 90 N,N,N,N-Tetramethylporphyrinogens, 349 Tetramethylurea, for porphyrin metalla- tions, 408 porphyrin esterification, 576

Tris(triphenylphosphine)chlororhodium, decarbonylation of formylpyrroles, 1 63

meso-Tetra(pentahalophenyl)porphyrins, 89

meso-Tetraphenylchlorin, 8 9 meso -Tetraphenylporphyrin Tripyrrenes, from dipyrrylmethanes, 254

Tripyrrins, nomenclature, 17 Tungsten porphyrins

synthesis, 89 X-ray structure, 399

infrared spectra, 445 2HC1 X-ray structure, 401 meso -Tetra(p-tolyl)-porphyrin synthesis, 441

Turacin, 318 diprotonated electronic spectrum, 415 electronic spectrum, 415 meso -Tetrasubstituted porphyrins, chromatography

column, 572 U tlc, 571

Thallium(III) nitrate, introduction of acetate a-Unsubstituted biladienes-ac cyclization to porphyrins, 248 synthesis, 248

into pyrrole, 127 Thallium porphyrins, 429 1-Thioformylbilenes-/?, 257 Thorium porphyrins, 436

5-Unsubstituted-2-formy !pyrroles, synthesis, 151

Uranium bis phthalocyanine, X-ray struc- ture, 399 Urobilin, nomenclature, 18 Urobilinogen, nomenclature, 18 Urohemin, pyridine hemochrome, elec- tronic spectrum, 316 Uroporphyrin chromatography, 560 nomenclature, 5, 7

X

Xanththoporphyrinogen, reduction, 277 X-ray structures N-alkylcorroles, 358 antimony octaethylporphyrin, 437 boron octaethylporphyrin

[(B2O(OR)2(OEP)], 399 cobalt TV-methyl meso-tetraphenyl-

''separation" by paper chromatography, 565

porphyrin, 356 N-ethoxycarbonylmethylporphyrin, 346 hafnium octaethylporphyrin, 436 iron protoporphyrin chloride, 396 iron meso-tetraphenylporphyrin-m-oxo

Uroporphyrin I, preparation, 318 Uroporphyrin I octamethyl ester, electronic spectrum, 316 Uroporphyrin III, isolation, 318 Uroporphyrin III octamethyl ester, elec- tronic spectrum, 316 Uroporphyrinogen I, decarboxylation, 280

dimer, 400

N-methylcorrole, 358

molybdenum porphyrins, 444

molybdenum-meso-tetraphenylporphyrin

dioxo complex, 398 nickel octaethylporphyrin, 396 niobium octaethylporphyrin, 436 niobium meso -tetraphenylporphyrin

V

Vanadyl deoxophylloerythroetioporphyrin in petroleum and shale, 486 X-ray structure, 487 Vanadyl porphyrins, 435 geochemical, 513, 517 Verdohemins, conversion to monazapor-

(Nb2O3TPPMOO niobium meso-tetraphenylporphyrin-oxo

complex, 398 octaethylporphyrin-HI3, 401 oxygenated picket fence, 456 phthalocyanines, 376 rhenium porphyrins, 447 bis(rhenium-tricarbonyl)m£S6>-tetra-

phyrins, 366 Vibrational spectroscopy, see Infrared spec- troscopy Vilsmeier-Haack copper deuteroporphyrins, 302 deuterohemin, 302

phenylporphyrin, 399 bis(rhodium dicarbonyl)octaethylpor-

phyrin, 399 rhodium N-methyloctaethylporphyrin,

formylation of dipyrrylmethanes, 180, 182 formylation of pyrroles, 146 pyrrylketone formation, 267 Vinyl porphyrins synthesis, 244, 281 from acetyl, 281 from aminoethyl, 281 from hydroxyethyl, 281 Vinyl pyrroles, 121 Violins, nomenclature, 19

346

N-substituted porphyrins, 363

technetium porphyrins, 447

meso -tetraphenylporphyrin 2HC1,

401

meso -tetraphenylporphyrin-free base,

399

tin octaethylporphyrin, 437

tin meso -tetraphenylporphyrin, 437

tin meso -tetraphenylporphyrin dichlo-

ride, 397 titanium- meso -tetraphenylporphyrin oxo

complex, 397 uranium phthalocyanines, 399 vanadyl deoxophylloerythroetioporphy-

W

Water soluble porphyrins, chromatography column, 573 tlc, 573

rin, 487 zirconium octaethylporphyrin, 436

zirconium octaethylporphyrin diacetate,

398

Zinc porphyrins, 425 ring oxidations, 427 synthesis, 427 Zinc meso –tetra (p-tolyl)-porphyrin,

Y

electronic spectrum, 415 Zirconium (acac)4, 404 Zirconium octaethylporphyrin, X-ray

Ytterbium porphyrins, 431 reconstitution with apomyoglobin, 431

Yttrium porphyrins, 431, 432 structure, 436

Zirconium octaethylporphyrin diacetate, Z

Zinc octaethylporphyrin, electronic spectrum, 414

X-ray structure, 398 Zirconium porphyrins, 436