correction. protic acid catalyzed thiono-thiolo rearrangements of phosphorus esters

2
Additions and Co~~ectio~s Vol. 37,1972 Stanley J. Padegimas and Peter Kovacic*: endo-7-Amino- methylbicyclo[3.3.1]nonan-3-ones from Rearrangement of 1-N- Substituted N-Haloadamantanamines by Aluminum Chloride. Page 2676, column 2, line 25. “JBX = 15 Hz” should be JBX 11 Hz. Vol. 38,1973 Lawrence R. Green* and Jack Hine: Isobutyraldehyde. The Page 2802. In the last full sentence the words “absence” and Page 2803, line 5. ‘‘0.337’’ should be 0.454. Kinetics of Acid- and Base-Catalyzed Equilibrations in Water. “presence” should be exchanged. Vol. 39,1974 John A. Tennis,* Thomas A. Wnuk, Michael J. Dolan, and Peter Kovacic*: Behavior of endo-7-Aminomethylbicyclo[3.3.1]- nonan-%one under Reducing Conditions. Page 768. Experimental Section, column 1, line 16. “0.48” should be 0.048. Column 2, line 3. “JBX = 16 Hz” should be JBX IL 11 Hz. Frank I. Carroll,* Gordon N. Mitchell, Joseph T. Blackwell, Asha Sobti, and Ronald Meck Configuration and Conformation of cis- and trans -3,S-Dimethylvalerolactones. Page 3895, column 1. Line 17. “I” should be 11. Line 25. “11” should be I. Line 27. “I” should be 11. Vol. 40, 1975 Thomas A. Wnuk, John A. Tonnis,* Michael J. Dolan, Stanley J. Padegimas, and Peter Kovacic*: Diazotization of endo-7-Ami- nomethylbicyclo[3.3.l]nonan-3-ols and endo-7-Aminomethylbicy- clo[3.3.l]non-2-ene. Page 447, column 2, line 9. “Z04” should be lo4. Page 448, column 1, line 11. “JBX = 13-14 Hz” should be JBX = Rodger N. Jenkins and Leon D. Freedman*: Dihydropheno- Page 768. Column 1, line 1. The letters “aoton” should be a pro- Page 768. Column 2, line 30. “8.2 g” should be 2.0 g. John A. Myers,* Wendell W. Wilkerson, and Samuel L. Council: 1,3-Dipolar Addition of an Oxazolium 5-Oxide to Cyclo- pentadienequinone and to Anthracenequinone. Page 2875, column 2. The structure assigned to compound 9 is in- correct. A structure in better accord with the available evidence is that shown below. The authors acknowledge Dr. R. S. Atkinson for first suggesting the discrepancy. 10-11 Hz. phosphazine Ring System. ton. Page 2876. Because the structure of 9 was incorrect, Scheme I is also incorrect. Peter Beak,* Jira Yamamoto, and Charles J. Upton: Hetero- philio Additions to Carbonyls and Thiocarbonyls. Scope and Stere- ochemistry. Page 3056, column 1. Lines 24 and 25 should read as follows. in- creased for the products from the other isomer. However, the value of K which accounts for the observed 82% retention found for the first experiment in Table I1 leads to a prediction of 69% retention for the second experiment in the table. Conversely, a value of K which ac- commodates the observed 120% retention in the second experiment leads to a prediction of 50% retention for the first experiment in the table. Accordingly, the predicted extent of. Page 3056, column 2, line 49. “100%” should be replaced by 67%. C. Max Hull* and Thomas W. Bargar: Transfer of Oxygen to Organic Sulfides with Dimethyl Sulfoxide Catalyzed by Hydrogen Chloride. Preparation of Disulfoxides. Page 3152. By-line. “Thomas W. Bargar” should be Thomas M. Bargar. Page 3154. Reference 12a should have cited H. Nieuwenhuyse and R. Louw, J. Chern. Soc., Perkin Trans. 1,839 (1973), which reverses these authors’ previous assignment of configurations for 1,2-bis- (methylsulfiny1)ethane (1); accordingly, they find that the CY form is actually the meso diastereoisomer. Vol. 41, 1976 Williadn F. Berkowitz* and Seth C. Grenetz: Cycloaddition of an Enamine to an Activated Cyclopropane. Page 13, ref 12. The carbethoxylation of 3,3-dimethylcyclopenta- none 16 was done using the procedure of A. P. Krapcho, J. Diamanti, C. Cayen, and R. Bingham, “Organic Syntheses”, Collect. Vol. V, Wiley, New York, N.Y., 1973, p 198. Hanne Eggert, Craig L. VanAntwerp, Norman S. Bhacca, and Carl Djerassi*: Carbon-13 Nuclear Magnetic Resonance Spectra of Hydroxy Steroids. Pages 72-74. The following entries in Table I were interchanged: for compound 10, C-9 and C-14; for 21, C-1 and C-17; for 29, ‘2-14 and C-17. In Table I1 for 6P-AcO-Androstane, C-3 and C-4 should be re- versed. Table 111: for 5ct entry “0.0 (19) t’’ should be 3.9 (19) t; for 12P entry “1.2 (9) t” should be -1.2 (9) t. K. T. Potts* and J. L. Marshall: Thiazolo[3,4-b]indazole, a Ring-Fused Tetravalent Sulfur Thiazole System. Page 129. In structure 3, the group, SC(Ph)=NHZ-, shown in the upper left is in error and should be replaced by R (as shown in struc- ture 4). G. S. Bajwa, K. Darrell Berlin,* and H. A. Pohl: Synthesis of A2~2’-Bis(1,3-benzodithiolidene) Derivatives and Complex Salts Therefrom with 7,7,8,8-Tetracyanoquinodimethane. Pages 145 and 146. In the title as well as in the last line of the right column of page 145 and the fifth line of the left column of .page 146, the correct ending for the name is benzothiolidene. Richard Baltzly: Studies on Catalytic Hydrogenation. I. The In- fluence on Reaction Rates of the Metal-Carrier Ratio, of Solvents and Acidity. Page 925, Table 111, footnote a. The third word should be start- ing. Page 926, Table VII. The upper part of this table should have a subheading reading as follows: Cyclohexene, 0.1 mg of Rh. Richard Baltzly: Studies on Catalytic Hydrogenation. 11. Poi- soning by Nucleophiles. Page 932, Table V, column 5 of table. All exponents in this column should be -7 (the first three are given as -7 and the next four as 7). Pankaja K. Kadaba: Role of Protic and Dipolar Aprotic Solvents in Cycloaddition Reactions Involving Anionic l,3-Dipoles, Action of Inorganic Azides on Imidoyl Chlorides. Page 1073, column 2. In structure A, the bonding between the C1 and C and between C and the N of azide should be shown as dotted lines rather than as solid lines. Vinayakam Subramaqyam,* Eileen H. Silver, and Albert H. Soloway: Reaction of Phosphoranes with Formate Esters. A New Method for Synthesis of Vinyl Ethers. Page 1272. It is regretted that, at the time of writing the paper, the authors were unaware of Dr. LeCorre’s work [Bull. SOC. Chirn. Fr., Nos. 9-10, 2005 (1974); C. R. Acad. Sci. Paris, 963 (1973)] showing that vinyl ethers are formed when the two stabilized phosphoranes, benzylidene and ethoxycarbonylmethylene, react with formate es- ters. Wojciech J. Stec,* Bogdan Uznariski, Karol Bruzik, and Jan Michalski*: Protic Acid Catalyzed Thiono-Thiolo Rearrangements of Phosphorus Esters. 4051

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Page 1: Correction. Protic Acid Catalyzed Thiono-Thiolo Rearrangements of Phosphorus Esters

Additions and C o ~ ~ e c t i o ~ s Vol. 37,1972

Stanley J. Padegimas and Peter Kovacic*: endo-7-Amino- methylbicyclo[3.3.1]nonan-3-ones from Rearrangement of 1-N- Substituted N-Haloadamantanamines by Aluminum Chloride.

Page 2676, column 2, line 25. “JBX = 15 Hz” should be JBX 11 Hz.

Vol. 38,1973 Lawrence R. Green* and Jack Hine: Isobutyraldehyde. The

Page 2802. In the last full sentence the words “absence” and

Page 2803, line 5. ‘‘0.337’’ should be 0.454.

Kinetics of Acid- and Base-Catalyzed Equilibrations in Water.

“presence” should be exchanged.

Vol. 39,1974 John A. Tennis,* Thomas A. Wnuk, Michael J. Dolan, and

Peter Kovacic*: Behavior of endo-7-Aminomethylbicyclo[3.3.1]- nonan-%one under Reducing Conditions.

Page 768. Experimental Section, column 1, line 16. “0.48” should be 0.048. Column 2, line 3. “JBX = 16 Hz” should be JBX IL 11 Hz.

Frank I. Carroll,* Gordon N. Mitchell, Joseph T. Blackwell, Asha Sobti, and Ronald Meck Configuration and Conformation of cis- and trans -3,S-Dimethylvalerolactones.

Page 3895, column 1. Line 17. “I” should be 11. Line 25. “11” should be I. Line 27. “I” should be 11.

Vol. 40, 1975 Thomas A. Wnuk, John A. Tonnis,* Michael J. Dolan, Stanley

J. Padegimas, and Peter Kovacic*: Diazotization of endo-7-Ami- nomethylbicyclo[3.3.l]nonan-3-ols and endo-7-Aminomethylbicy- clo[3.3.l]non-2-ene.

Page 447, column 2, line 9. “Z04” should be lo4. Page 448, column 1, line 11. “JBX = 13-14 Hz” should be JBX =

Rodger N. Jenkins and Leon D. Freedman*: Dihydropheno-

Page 768. Column 1, line 1. The letters “aoton” should be a pro-

Page 768. Column 2, line 30. “8.2 g” should be 2.0 g.

John A. Myers,* Wendell W. Wilkerson, and Samuel L. Council: 1,3-Dipolar Addition of an Oxazolium 5-Oxide to Cyclo- pentadienequinone and to Anthracenequinone.

Page 2875, column 2. The structure assigned to compound 9 is in- correct. A structure in better accord with the available evidence is that shown below. The authors acknowledge Dr. R. S. Atkinson for first suggesting the discrepancy.

10-11 Hz.

phosphazine Ring System.

ton.

Page 2876. Because the structure of 9 was incorrect, Scheme I is also incorrect.

Peter Beak,* Jira Yamamoto, and Charles J. Upton: Hetero- philio Additions to Carbonyls and Thiocarbonyls. Scope and Stere- ochemistry.

Page 3056, column 1. Lines 24 and 25 should read as follows. in- creased for the products from the other isomer. However, the value of K which accounts for the observed 82% retention found for the first experiment in Table I1 leads to a prediction of 69% retention for the second experiment in the table. Conversely, a value of K which ac- commodates the observed 120% retention in the second experiment leads to a prediction of 50% retention for the first experiment in the table. Accordingly, the predicted extent of.

Page 3056, column 2, line 49. “100%” should be replaced by 67%.

C. Max Hull* and Thomas W. Bargar: Transfer of Oxygen to Organic Sulfides with Dimethyl Sulfoxide Catalyzed by Hydrogen Chloride. Preparation of Disulfoxides.

Page 3152. By-line. “Thomas W. Bargar” should be Thomas M. Bargar.

Page 3154. Reference 12a should have cited H. Nieuwenhuyse and R. Louw, J. Chern. Soc., Perkin Trans. 1,839 (1973), which reverses these authors’ previous assignment of configurations for 1,2-bis- (methylsulfiny1)ethane (1); accordingly, they find that the CY form is actually the meso diastereoisomer.

Vol. 41, 1976 Williadn F. Berkowitz* and Seth C. Grenetz: Cycloaddition of

an Enamine to an Activated Cyclopropane. Page 13, ref 12. The carbethoxylation of 3,3-dimethylcyclopenta-

none 16 was done using the procedure of A. P. Krapcho, J. Diamanti, C. Cayen, and R. Bingham, “Organic Syntheses”, Collect. Vol. V, Wiley, New York, N.Y., 1973, p 198.

Hanne Eggert, Craig L. VanAntwerp, Norman S. Bhacca, and Carl Djerassi*: Carbon-13 Nuclear Magnetic Resonance Spectra of Hydroxy Steroids.

Pages 72-74. The following entries in Table I were interchanged: for compound 10, C-9 and C-14; for 21, C-1 and C-17; for 29, ‘2-14 and C-17. In Table I1 for 6P-AcO-Androstane, C-3 and C-4 should be re- versed. Table 111: for 5ct entry “0.0 (19) t’’ should be 3.9 (19) t; for 12P entry “1.2 (9) t” should be -1.2 (9) t.

K. T. Potts* and J. L. Marshall: Thiazolo[3,4-b]indazole, a Ring-Fused Tetravalent Sulfur Thiazole System.

Page 129. In structure 3, the group, SC(Ph)=NHZ-, shown in the upper left is in error and should be replaced by R (as shown in struc- ture 4).

G. S. Bajwa, K. Darrell Berlin,* and H. A. Pohl: Synthesis of A2~2’-Bis(1,3-benzodithiolidene) Derivatives and Complex Salts Therefrom with 7,7,8,8-Tetracyanoquinodimethane.

Pages 145 and 146. In the title as well as in the last line of the right column of page 145 and the fifth line of the left column of .page 146, the correct ending for the name is benzothiolidene.

Richard Baltzly: Studies on Catalytic Hydrogenation. I. The In- fluence on Reaction Rates of the Metal-Carrier Ratio, of Solvents and Acidity.

Page 925, Table 111, footnote a. The third word should be start- ing.

Page 926, Table VII. The upper part of this table should have a subheading reading as follows: Cyclohexene, 0.1 mg of Rh.

Richard Baltzly: Studies on Catalytic Hydrogenation. 11. Poi- soning by Nucleophiles.

Page 932, Table V, column 5 of table. All exponents in this column should be -7 (the first three are given as -7 and the next four as 7).

Pankaja K. Kadaba: Role of Protic and Dipolar Aprotic Solvents in Cycloaddition Reactions Involving Anionic l,3-Dipoles, Action of Inorganic Azides on Imidoyl Chlorides.

Page 1073, column 2. In structure A, the bonding between the C1 and C and between C and the N of azide should be shown as dotted lines rather than as solid lines.

Vinayakam Subramaqyam,* Eileen H. Silver, and Albert H. Soloway: Reaction of Phosphoranes with Formate Esters. A New Method for Synthesis of Vinyl Ethers.

Page 1272. It is regretted that, at the time of writing the paper, the authors were unaware of Dr. LeCorre’s work [Bull. SOC. Chirn. Fr., Nos. 9-10, 2005 (1974); C. R. Acad. Sci. Paris, 963 (1973)] showing that vinyl ethers are formed when the two stabilized phosphoranes, benzylidene and ethoxycarbonylmethylene, react with formate es- ters.

Wojciech J. Stec,* Bogdan Uznariski, Karol Bruzik, and Jan Michalski*: Protic Acid Catalyzed Thiono-Thiolo Rearrangements of Phosphorus Esters.

4051

Page 2: Correction. Protic Acid Catalyzed Thiono-Thiolo Rearrangements of Phosphorus Esters

4052 J. Org. Chem., Vol. 41, No. 25, 1976 Additions a n d Corrections

Page 1291, column 2, bottom. 1 + H+ - 5 should be 1 + Hf * 5.

Charles D. Hufford* and William L. Lasswell, Jr.: Uvaretin and Isouvaretin. Two Novel Cytotoxic C-Benzylflavanones from Uuariu chamae L.

Page 1297. The name uvaretin has also been chosen for a C-ben- zylated dihydrochalcone from another species of Uuaria: J. R. Cole, S. J. Torrance, R. M. Weidhopf, S. K. Arora, and R. B. Bates, J. Org. Chem., 41,1852 (1976). Since the received date of our communication was later than that of Cole et al., we have agreed to change the names of our flavanones from uvaretin to chamanetin and isouvaretin to isochamanetin. The correct botanical authority for Uuaria chamae is P. Beauv.

Samuel P. McManus,* P. Judson Kelly, William J. Patterson, and Charles U. Pittman, Jr.: Reaction of Lactones and Thiolactones with 2-Amino-2-methyl-1-propanol. Synthesis and 2-Substituted 2-Oxazolines.

Page 1643, Table I. The calculated values for the elemental analysis of 5a are incorrect. The values for C, H, and N should be 61.12,9.62, and 8.91, respectively.

Toshiaki Yoshimura, Tetsuo Omata, Naomiohi Furukawa,* and Shigeru Oae: Preparation and Physical and Chemical Properties of “Free” Sulfilimines.

Page 1729. Table I: run 7, before (35-36)c the number 80 should be added; run 10, the number 55 should be moved down to run 11; run 19, after 95 (191) the superscript d should be added; footnote e , “mp 111 “C” should be corrected to mp 104 OC. Column 1. In lines 5 and 6, “(runs 9,14)” should be corrected to (runs 10,15). In line 18, “(runs 10,12, 13, 15;18)” should be corrected to (runs 11,13,14,16-19).

Page 1730. In Table 11, after P - C H ~ C ~ H ~ c-C~HS (cyclopropyl) should be added. Column 1. In line 13, the numbers “11,19” should

be corrected to 12,20. In paragraph 3, lines 10 and 11, “longer wave- length” should be corrected to higher wavenurnber.

H.-G. Heine,* W. Hartmann, F. D. Lewis, and R. T. Lauterbach

Page 1908. The structures of ketones 1 and 2 in Table I should ap- Photochemical Reactivity of Some Bridgehead Phenyl Ketpnes.

pear as follows:

1 2 Sergio Alunni, Enrico Baciocchi,* and Piero Perucci: Kinetic

Study of Elimination Reactions Promoted by Crown Ether Com- plexed Potassium tert-Butoxide in tert-Butyl Alcohol.

Page 2637. In Table 11, line 21 should read as follows: 2 , 2 4 (Sub- strate); 30 (Temp, “C); 1.09 X low2 ([t-BuOK], M); 2.31 X ([18C6], M); 0.31 (kz, MI1 s-’).

4. Page 2638, column 2. In footnote 7, line 2, “ref 3” should be ref

Shyam K. Gupta: New Reactions and Reagents. 5. Ketalizntion of 1,3-Dihydroxy-2-propane with Alltanols. Formation of Acyclic and Cyclic Ethers Derived from Pyruvic Aldehyde.

Page 2646, ref 18. We wish to call at,tention to two additional ref- erences pertaining to work described earlier by J. Gelas: J. Gelas and A. Thialliers, Carbohydr. Res., 30,21 (1973), and J. Gelas, P. Calinaud, D. Horton, and J. D. Wander, J. Chern. Soc., Perkin Trans. 2, 1145 (1974).