huang wittigolefinatnusingph3pch2oh siexp...experimental tricyclohexyl(hydroxymethyl)phosphonium...

Supporting Information

In situ generation of formaldehyde and triphenylphosphine from

(hydroxymethyl)triphenylphosphonium and its application in Wittig

olefination

Wenhua Huang* and Jie Xu

Department of Chemistry, Tianjin University, 92 Weijin Road, Tianjin 300072, P. R. China.

Email: [email protected].

Table of Contents Page Tricyclohexyl(hydroxymethyl)phosphonium tetrafluoroborate (1d)…….... S2 NMR data of 3a-e…...…………………………………………………….. S2 NMR data of 3f-l………………………………………………………… S3 NMR data of 3m-p………………………………………………………… S4 Acknowledgement………………………………………………………… S4 References………………………………………………………………… S4 NMR spectra of 1d………………………………………………………… S6-8 NMR spectra of 3a…………………………………………………………. S9-10 NMR spectra of 3b………………………………………………………… S11-12NMR spectra of 3c…………………………………………………………. S13-14NMR spectra of 3d………………………………………………………… S15-16NMR spectra of 3e…………………………………………………………. S17-18NMR spectra of 3f…………………………………………………………. S19-20NMR spectra of 3g…………………………………………………………. S21-22NMR spectra of 3h………………………………………………………. S23-24NMR spectra of 3i…………………………………………………………. S25-26NMR spectra of 3j…………………………………………………………. S27-28NMR spectra of 3k………………………………………………………. S29-30NMR spectra of 3l…………………………………………………………. S31-32NMR spectra of 3m………………………………………………………. S33-34NMR spectra of 3n………………………………………………………. S35-36NMR spectra of 3o…………………………………………………………. S37-38NMR spectra of 3p………………………………………………………. S39-40

1S

EXPERIMENTAL

Tricyclohexyl(hydroxymethyl)phosphonium tetrafluoroborate (1d)

A solution of HBF4 in water (40 w%, 11.152 g, 0.05 mol) was added dropwise to a mixture of tricyclohexylphosphine (5.609 g, 0.02 mmol), paraformaldehyde (0.601 g, 0.02 mol) and ether (20 mL) in a round-bottom flask (100 mL). After stirred at rt for 16 h, the reaction mixture was evaporated to remove ether, diluted with water (30 mL), and then extracted with CH2Cl2 (30 mL x 2). The combined extracts were dried over anhydrous MgSO4, evaporated to dryness, and then treated with tert-buty methylether. The resulting precipitates were collected by filtration, and dried in vacuo to afford 1d (4.334 g, 54%). A white solid, mp 134-137 C; 1H-NMR (400 MHz, CDCl3) 1.25-1.50 (m, 9 H), 1.55-1.70 (m, 6 H), 1.77-1.83 (m, 3 H), 1.90-2.04 (m, 12 H), 2.40-2.53 (m, 3 H), 4.32 (brs, 1 H), 4.62 (s, 2 H). 13C-NMR (100 MHz, CDCl3) 50.8 (d, JC-P = 59.0 Hz), 28.7 (d, JC-P = 38.5 Hz), 26.6 (d, JC-P = 4.0 Hz). 26.5 (d, JC-P = 11.7 Hz), 25.3. 31P-NMR (162 MHz, CDCl3) 28.78. HRMS-ESI (positive) m/z: calcd for C19H36OP+ (1d-cation), 311.2498; found, 311.2499.

2-Vinylnaphthalene (3a)

A white solid, yield: 66.8 mg, 87%; Rf = 0.53 (PE); mp 62-64 (lit.1 64-66); 1H-NMR (600 MHz, CDCl3) 5.32 (d, J = 10.9 Hz, 1 H), 5.85 (d, J = 17.6 Hz, 1 H), 6.86 (dd, J = 10.9, 17.6 Hz, 1 H), 7.39-7.45 (m, 2 H), 7.62 (d, J = 8.5 Hz, 1 H), 7.72 (s, 1 H), 7.75-7.79 (m, 3 H). 13C-NMR (151 MHz, CDCl3) 137.0, 135.0, 133.6, 133.2, 128.2, 128.1, 127.7, 126.4, 126.3, 125.9, 123.2, 114.2.

1-Methoxy-4-vinylbenzene (3b)2

A colorless oil, yield: 46.8 mg, 73%; Rf = 0.66 (CCl4); 1H-NMR (600 MHz, CDCl3) 3.80 (s, 3 H), 5.12 (d, 1 H, J = 10.9 Hz), 5.61 (d, 1 H, J = 17.5 Hz), 6.66 (dd, 1 H, J = 10.9, 17.5 Hz), 6.86 (d, 2 H, J = 8.0 Hz), 7.34 (d, 2 H, J = 8.0 Hz). 13C-NMR (151 MHz, CDCl3) 159.3, 136.2, 130.4, 127.4, 113.9, 111.6, 55.3.

1-Methyl-4-vinylbenzene (3c)1

A colorless oil, yield: 46.8 mg, 79%; Rf = 0.77 (PE); 1H-NMR (400 MHz, CDCl3) 2.39 (s, 3 H), 5.23 (d, 1 H, J = 10.9 Hz), 5.75 (d, 1 H, J = 17.6 Hz), 6.74 (dd, 1 H, J = 10.9, 17.6 Hz), 7.18 (d, 2 H, J = 7.9 Hz), 7.36 (d, 2 H, J = 8.0 Hz). 13C-NMR (100 MHz, CDCl3) 137.6, 136.7, 134.8, 129.2, 126.1, 112.7, 21.2.

1-(tert-Butyl)-4-vinylbenzene (3d)3

A colorless oil, yield: 63.0 mg, 79%; Rf = 0.55 (PE); 1H-NMR (600 MHz, CDCl3) 1.31 (s, 9 H), 5.19 (d, 1 H, J = 10.9 Hz), 5.70 (d, 1 H, J = 17.6 Hz), 6.69 (dd, 1 H, J = 10.9, 17.6 Hz), 7.35 (s, 4 H). 13C-NMR (151 MHz, CDCl3) 150.9, 136.6, 134.8, 125.9, 125.4, 113.0, 34.6, 31.3.

1,4-Divinylbenzene (3e)3

In this case, 1a (1.0 mmol) and K2CO3 (2.0 mmol) was used. A pale yellow semi-

2S

solid, yield: 45.1 mg, 69%; Rf = 0.54 (PE); 1H-NMR (600 MHz, CDCl3) 5.23 (d, 2 H, J = 10.9 Hz), 5.74 (d, 2 H, J = 17.6 Hz), 6.70 (dd, 2 H, J = 10.9, 17.6 Hz), 7.37 (s, 4 H). 13C-NMR (151 MHz, CDCl3) 137.1, 136.4, 126.4, 113.7.

(E)-Buta-1,3-dien-1-ylbenzene (3f)1

A pale yellow oil, yield: 53.1 mg, 82%; Rf = 0.58 (PE); 1H-NMR (400 MHz, CDCl3), 5.25 (d, 1 H, J = 10.1 Hz), 5.41 (d, 1 H, J = 16.9 Hz), 6.53-6.68 (m, 2 H), 6.87 (dd, 1 H, J = 10.5, 15.6 Hz), 7.30 (t, 1 H, J = 7.3 Hz), 7.36-7.42 (m, 2 H), 7.48 (d, 2 H, J = 7.4 Hz). 13C-NMR (100 MHz, CDCl3) 137.17, 137.15, 132.8, 129.6, 128.6, 127.6, 126.4, 117.5.

Buta-1,3-dien-2-ylbenzene (3g)4

A pale yellow oil, yield: 40.0 mg, 61%; Rf = 0.61 (PE); 1H-NMR (400 MHz, CDCl3) 5.19-5.27 (m, 3 H), 5.34 (s, 1 H), 6.66 (dd, 1 H, J = 10.9, 17.3 Hz), 7.31-7.41 (m, 5 H). 13C-NMR (100 MHz, CDCl3) 148.2, 139.7, 138.1, 128.2, 128.1, 127.4, 117.1, 116.8.

1-Bromo-4-vinylbenzene (3h)3

A pale yellow oil, yield: 80.2 mg, 88%; Rf = 0.54 (PE); 1H-NMR (600 MHz, CDCl3) 5.26 (d, 1 H, J = 10.9 Hz), 5.73 (d, 1 H, J = 17.6 Hz), 6.64 (dd, 1 H, J = 10.9, 17.6 Hz), 7.25 (d, 2 H, J = 8.4 Hz), 7.43 (d, 2 H, J = 8.4 Hz). 13C-NMR (151 MHz, CDCl3) 136.4, 135.7, 131.6, 127.7, 121.6, 114.6.

1-Chloro-4-vinylbenzene (3i)1

A colorless oil, yield: 55.9 mg, 81%; Rf = 0.70 (PE); 1H-NMR (400 MHz, CDCl3) 5.30 (d, 1 H, J = 10.9 Hz), 5.76 (d, 1 H, J = 17.5 Hz), 6.70 (dd, 1 H, J =10.9, 17.5 Hz), 7.31-7.38 (m, 4 H). 13C-NMR (100 MHz, CDCl3) 136.0, 135.6, 133.4, 128.6, 127.4, 114.4.

Methyl 4-vinylbenzoate (3j)1

A white semi-solid, yield: 69.2 mg, 85%; Rf = 0.30 (PE: EtOAc 25:1); 1H-NMR (400 MHz, CDCl3) 3.91 (s, 3 H), 5.38 (d, 1 H, J = 10.9 Hz), 5.86 (d, 1 Hz, J = 17.6 Hz), 6.75 (dd, 1 H, J = 10.9, 17.6 Hz), 7.46 (d, 2 H, J = 8.3 Hz), 8.00 (d, 2 H, J = 8.3 Hz). 13C-NMR (100 MHz, CDCl3) 166.8, 141.9, 136.0, 129.8, 129.2, 126.1, 116.4, 52.0.

4-Vinylbenzonitrile (3k)1

A colorless oil, yield: 55.0 mg, 85%; Rf = 0.24 (PE: EtOAc 25:1); 1H-NMR (600 MHz, CDCl3) 5.45 (d, 1 H, J = 10.9 Hz), 5.88 (d, 1 H, J = 17.6 Hz), 6.73 (dd, 1 H, J = 10.9, 17.6 Hz), 7.49 (d, 2 H, J = 8.2 Hz), 7.62 (d, 2 H, J = 8.2 Hz). 13C-NMR (151 MHz, CDCl3) 141.9, 135.3, 132.4, 126.7, 118.9, 117.7, 111.1.

2-Vinylbenzonitrile (3l)1

A colorless oil, yield: 55.9 mg, 87%; Rf = 0.48 (PE: EtOAc 25:1); 1H-NMR (600 MHz, CDCl3) 5.53 (d, 1 H, J = 11.0 Hz), 5.95 (d, 1 H, J = 17.4 Hz), 7.07 (dd, 1 H, J

3S

= 11.0, 17.4 Hz), 7.34 (t, 1 H, J = 7.7 Hz), 7.56 (t, 1 H, J = 7.7Hz), 7.62 (d, 1 H, J = 7.7 Hz), 7.67 (d, 1 H, J = 7.7 Hz). 13C-NMR (151 MHz, CDCl3) 140.6, 132.9, 132.8, 132.7, 127.9, 125.4, 118.9, 117.7, 111.1.

1-Nitro-4-vinylbenzene (3m)1

A yellow oil, yield: 65.3 mg, 88%; Rf = 0.33 (PE: EtOAc 25:1); 1H-NMR (600 MHz, CDCl3) 5.41 (d, 1 H, J = 10.9 Hz), 5.84 (d, 1 H, J = 17.6 Hz), 6.69 (dd, 1 H, J = 10.9, 17.6 Hz), 7.44 (d, 2 H, J = 8.8 Hz), 8.09 (d, 2 H, J = 8.8 Hz). 13C-NMR (151 MHz, CDCl3) 147.1, 143.8, 134.9, 126.8, 123.9, 118.6,

1-Nitro-2-vinylbenzene (3n)5

A yellow oil, yield: 66.1 mg, 89%; Rf = 0.31 (PE: EtOAc 25:1); 1H-NMR (600 MHz, CDCl3) 5.48 (d, 1 H, J = 11.0 Hz), 5.75 (d, 1 H, J = 17.3 Hz), 7.17 (dd, 1 H, J = 11.0, 17.3 Hz), 7.38-7.45 (m, 1 H), 7.56-7.60 (m, 1 H), 7.63 (d, 1 H, J = 7.8 Hz), 7.92 (d, 1H, J = 8.2 Hz). 13C-NMR (151 MHz, CDCl3) 147.8, 133.3, 133.1, 132.4, 128.5, 128.3, 124.4, 118.9.

1-Nitro-3-vinylbenzene (3o)6

A yellow oil, yield: 65.4 mg, 88%; Rf = 0.10 (PE); 1H-NMR (600 MHz, CDCl3) 5.44 (d, 1 H, J = 10.9 Hz), 5.90 (d, 1 H, J = 17.6 Hz), 6.76 (dd, 1 H, J = 10.9, 17.6 Hz), 7.49 (t, 1 H, J = 7.9 Hz),7.71 (d, 1 H, J = 7.9 Hz), 8.10 (d, 1 H, J = 7.9 Hz), 8.24 (s, 1 H). 13C-NMR (151 MHz, CDCl3) 148.5, 139.2, 134.7, 132.1, 129.4, 122.4, 120.8, 117.0.

Phenyl(4-vinylphenyl)methanone (3p)7

A pale yellow oil, yield: 91.0 mg, 87%; Rf = 0.12 (PE: EtOAc 25:1); 1H-NMR (600 MHz, CDCl3) 5.38 (d, 1 H, J = 10.9 Hz), 5.87 (d, 1 H, J = 17.6 Hz), 6.76 (dd, 1 H, J = 10.9, 17.6 Hz), 7.44-7.51 (m, 4 H), 7.54-7.59 (m, 1 H), 7.76-7.80 (m, 4 H). 13C-NMR (151 MHz, CDCl3) 196.1, 141.5, 137.7, 136.6, 136.0, 132.3, 130.5, 129.9, 128.3, 126.0, 116.6.

ACKNOWLEDGEMENT

We thank the National Natural Science Foundation of China for their financial support of our program (Grant No. 21272170)

REFERENCES

(1) Smith, C. R.; RajanBabu, T. V. Tetrahedron 2010, 66, 1102‐1110.

(2) Iwasaki, T.; Miyata, Y.; Akimoto, R.; Fujii, Y.; Kuniyasu, H.; Kambe, N. J Am Chem Soc 2014,

136, 9260‐9263.

(3) Wienhofer, G.; Westerhaus, F. A.; Jagadeesh, R. V.; Junge, K.; Junge, H.; Beller, M. Chem

Commun 2012, 48, 4827‐4827‐4829.

(4) Chou, T. S.; Hung, S. C.; Tso, H. H. The Journal of Organic Chemistry 1987, 52, 3394‐3399.

(5) Joucla, L.; Cusati, G.; Pinel, C.; Djakovitch, L. Tetrahedron Lett 2008, 49, 4738‐4741.

(6) Lee, P. H.; Lee, S. W.; Seomoon, D. Org Lett 2003, 5, 4963‐4966.

4S

(7) Alacid, E.; Nájera, C. The Journal of Organic Chemistry 2009, 74, 8191‐8150.

5S

ppm (t1)0.01.02.03.04.05.06.07.08.09.0

7.29

8

4.62

3

4.31

94.

315

2.51

92.

488

2.45

72.

425

1.99

9

1.96

2

1.92

7

1.81

31.

787

1.65

91.

653

1.62

91.

599

1.57

41.

569

1.45

61.

425

1.39

41.

368

1.34

51.

314

1.28

3

0.00

9

2.00

0.88

3.23

13.543.756.80

10.48

1H-NMR (400 MHz, CDCl3)

P

OH

F4B-

1d

6S

ppm (t1)-100102030405060708090100110120130140150160170180190200210

77.4

2777

.108

76.8

6476

.790

51.0

4550

.458

28.8

9228

.509

26.6

3926

.599

26.5

4126

.424

25.3

26

13C-NMR (100 MHz, CDCl3)

P

OH

F4B-

1d

7S

ppm (t1)-200-150-100-50050100

28.7

81

31P-NMR (162 MHz, CDCl3)

P

OH

F4B-

1d

8S

ppm (t1)0.01.02.03.04.05.06.07.08.09.0

7.78

37.

771

7.75

6

7.72

17.

622

7.60

87.

447

7.43

77.

425

7.41

47.

402

7.18

4

6.88

36.

865

6.85

46.

836

5.86

85.

839

5.32

55.

306

1.46

2

1.24

8

1.00

1.00

0.97

2.020.990.973.05


3a

9S

ppm (t1)-100102030405060708090100110120130140150160170180190200210

137.

013

5.1

133.

613

3.2

128.

212

8.1

127.

7

126.

512

6.3

126.

0

123.

211

4.2

77.3

77.1

76.9


3a

10S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

7.35

07.

336

6.86

26.

849

6.68

16.

663

6.65

26.

634

5.62

15.

591

5.12

85.

110

3.80

0

1.00

0.97

1.97

0.97

1.99

2.91


MeO

3b

11S

ppm (t1)050100150200

159.

4

136.

2

130.

4

127.

4

113.

911

1.6

77.3

77.1

76.9

55.3


MeO

3b

12S

ppm (t1)0.01.02.03.04.05.06.07.08.09.0

7.36

87.

347

7.19

17.

171

6.77

66.

749

6.73

26.

705

5.76

8

5.72

4

5.24

65.

219

2.39

0

3.00

1.00

1.01

0.98

1.981.99

1H-NMR ︵400 MHz, CDCl3 ︶ 3c

13S

ppm (t1)-100102030405060708090100110120130140150160170180190200210

137.

6

136.

713

4.9

129.

2

126.

1

112.

8

77.4

77.0

76.7

21.2

13C-NMR ︵100 MHz, CDCl3 ︶

3c

14S

ppm (t1)0.01.02.03.04.05.06.07.08.09.0

7.34

7

6.71

76.

699

6.68

86.

670

5.71

85.

689

5.19

55.

177

1.31

3

1.00

1.00

0.99

4.03

9.07


3d

15S

ppm (t1)050100150200

150.

9

136.

6

134.

9

126.

012

5.5

113.

1

77.3

77.1

76.9

34.6

31.3

13C-NMR ︵151 MHz, CDCl3 ︶3d

16S

ppm (t1)0.01.02.03.04.05.06.07.08.09.0

7.36

6

6.72

06.

702

6.69

16.

673

5.75

85.

728

5.24

25.

224

2.00

2.05

2.00

4.12

1H-NMR ︵600 MHz, CDCl3 ︶

3e

17S

ppm (t1)050100150200

137.

113

6.5

126.

4

113.

8

77.3

77.1

76.8


3e

18S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

7.49

17.

472

7.40

97.

391

7.37

2

7.32

17.

302

7.28

4

6.90

26.

876

6.86

36.

837

6.66

26.

635

6.62

26.

610

6.59

36.

584

6.56

76.

542

5.43

5

5.39

2

5.26

75.

242

1.001.02

1.98

0.98

1.032.021.95


3f

19S

ppm (t1)-100102030405060708090100110120130140150160170180190200210

137.

213

7.2

132.

9

129.

6

128.

6

127.

6

126.

4

117.

6

77.3

77.0

76.7


3f

20S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

7.40

57.

388

7.38

47.

370

7.36

57.

357

7.34

97.

337

7.32

77.

321

7.28

26.

693

6.66

66.

650

6.62

3

5.33

6

5.26

35.

250

5.23

95.

206

1.00

5.10

1.033.09


3g

21S

ppm (t1)110.0112.0114.0116.0118.0120.0122.0124.0126.0128.0130.0132.0134.0136.0138.0140.0142.0144.0146.0148.0150.0152.0154.0

148.

3

139.

7

138.

2

128.

312

8.1

127.

5

117.

1

116.

8


3g

22S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

7.43

97.

425

7.26

17.

246

6.66

16.

643

6.63

16.

613

5.74

15.

712

5.27

35.

255

1.00

0.97

0.99

2.021.94


Br

3h

23S

ppm (t1)050100150200

136.

513

5.8

131.

712

7.8

121.

6

114.

6

77.3

77.1

76.9


Br

3h

24S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

7.37

67.

371

7.35

57.

334

7.31

87.

313

6.73

86.

711

6.69

46.

667

5.78

0

5.73

6

5.31

75.

289

1.00

1.00

0.97

3.91


Cl

3i

25S

ppm (t1)-100102030405060708090100110120130140150160170180190200210

136.

113

5.7

133.

5

128.

7

127.

4

114.

5

77.3

77.0

76.7


Cl

3i

26S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

8.01

27.

991

7.46

87.

447

6.78

46.

757

6.74

06.

713

5.88

4

5.84

0

5.39

35.

366

3.91

2

1.00

1.00

3.05

0.97

2.00

1.95


MeOOC

3j

27S

ppm (t1)-100102030405060708090100110120130140150160170180190200210

166.

8

141.

9

136.

012

9.9

129.

3

126.

1

116.

4

77.4

77.1

76.8

52.0


MeOOC

3j

28S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

7.62

27.

608

7.49

37.

480

6.75

36.

735

6.72

46.

706

5.89

45.

865

5.46

05.

442

1.00

1.01

0.97

1.922.19

1H-NMR (CDCl3, 600 MHz)

NC

3k

29S

ppm (t1)050100150200

141.

9

135.

4

132.

412

6.8

118.

9

117.

8

111.

1

77.3

77.0

76.8


NC

3k

30S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

7.67

47.

661

7.62

37.

610

7.56

87.

555

7.54

27.

351

7.33

87.

326

7.26

87.

094

7.07

57.

065

7.04

6

5.96

05.

931

5.54

15.

523

1.00

0.98

0.95

0.97

0.951.010.93


CN

3l

31S

ppm (t1)-100102030405060708090100110120130140150160170180190200210

140.

6

132.

913

2.9

132.

8

128.

012

5.4

118.

9

117.

8

111.

1

77.3

77.1

76.9

13C-NMR (151 MH, CDCl3)

CN

3l

32S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

8.09

58.

080

7.44

97.

435

6.71

26.

694

6.68

36.

665

5.85

55.

826

5.41

95.

401

1.00

1.01

1.00

2.00

2.01


O2N

3m

33S

ppm (t1)050100150200

147.

2

143.

8

135.

0

126.

8

123.

9

118.

6

77.3

77.1

76.9


O2N

3m

34S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

7.92

77.

914

7.63

37.

620

7.59

37.

580

7.56

7

7.42

37.

421

7.41

07.

398

7.19

37.

174

7.16

47.

146

5.76

15.

732

5.49

25.

473

1.00

1.00

0.97

0.99

0.98

0.980.98


NO2

3n

35S

ppm (t1)050100150200

147.

9

133.

313

3.1

132.

512

8.5

128.

412

4.4

119.

0

77.3

77.1

76.9


NO2

3n

36S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

8.24

0

8.10

38.

089

7.71

27.

699

7.50

87.

495

7.48

2

6.78

86.

769

6.75

86.

740

5.91

05.

881

5.45

25.

434

1.00

0.97

0.95

0.95

0.96

0.900.93


O2N

3o

37S

(t1)-100102030405060708090100110120130140150160170180190200210

148.

6

139.

2

134.

7

132.

1

129.

5

122.

4

120.

911

7.1

77.3

77.1

76.9


O2N

3o

38S

ppm (t1)-1.00.01.02.03.04.05.06.07.08.09.0

7.78

67.

779

7.77

47.

772

7.76

57.

573

7.56

17.

548

7.53

6

7.49

27.

479

7.47

27.

459

7.44

7

7.24

8

6.78

56.

767

6.75

66.

738

5.88

75.

858

5.39

45.

375

1.00

1.02

1.00

1.104.09

4.04


O

3p

39S

ppm (t1)-100102030405060708090100110120130140150160170180190200210

196.

1

141.

613

7.8

136.

713

6.0

132.

4

130.

613

0.0

128.

312

6.1

116.

6

77.4

77.1

76.9


O

3p

40S

huang wittigolefinatnusingph3pch2oh siexp...experimental tricyclohexyl(hydroxymethyl)phosphonium...

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