April 2005
427
stage apparatus and are uncorrected. Mass spectra (MS) were recorded on a
JEOL JMP-DX300 instrument. H-NMR spectra were recorded on a JEOL 16) Yasuike S., Okajima S., Kurita J., Chem. Pharm. Bull., 50, 1404—
Asymmetry, 11, 4043—4047 (2000).
1
JNM-ECP500 (500 MHz) spectrometer in CDCl using tetramethylsilane as
1406 (2002).
3
an internal standard. Column chromatography was performed on Silica Gel
17) Yasuike S., Okajima S., Yamaguchi K., Seki H., Kurita J., Tetrahedron,
59, 4959—4966 (2003).
41)
6
0N (Kanto Chemical Co., Inc.). Tri(p-tolyl)- 2b (mp 128—131 °C, lit.
42)
127 °C), tri(p-fluorophenyl)stibane 2c (mp 93—95 °C, lit. 91.8 °C), tri(p- 18) Yasuike S., Okajima S., Yamaguchi K., Kurita J., Tetrahedron Lett., 44,
42)
chlorophenyl)stibane 2d (mp 102—104 °C, lit. 111.5 °C), tris(p-trifluo-
romethylphenyl)stibane 2e (mp 130—132 °C), and tri(p-ethoxycar- 19) Yasuike S., Kawara S., Okajima S., Seki H., Yamaguchi K., Kurita J.,
bonylphenyl)stibane 2f (mp 74—76 °C) were prepared by the reaction of Tetrahedron Lett., 45, 9139—9142 (2004).
SbCl or SbBr with appropriate Grignard reagents, and Ph SbO was ob- 20) Suzuki H., Ikegami T., Matano Y., Tetrahedron Lett., 35, 8197—8200
6217—6220 (2003).
43)
3
3
3
tained from Tokyo Kasei Kogyo Co., Ltd., Catalog No. T 1850.
(1994).
General Procedure for Oxidation of Benzoins To a stirred solution of
21) Suzuki H., Ikegami T., J. Chem. Res. (S), 1996, 24—25 (1996).
benzoin 1a (1 mmol) in CH Cl (4 ml) was added 2a (0.1 mmol) at room 22) Varma R. S., Kumar D., Dahiya R., J. Chem. Res. (S), 1998, 324—325
2
2
temperature under air. The mixture was stirred for 8—24 h at the same tem-
perature, and then concentrated in vacuo. The residue was purified by silica
gel column chromatography using hexane/ethyl acetate (for 3a, c, e),
CH Cl /hexane (for 3b, f, g) or CH Cl /ethyl acetate (for 3d) as eluents. The
(1998).
23) Jose B., Vishnu Unni M. V., Prathapan S., Vadakkan J. J., Synth. Com-
mun., 32, 2495—2498 (2002).
24) Tymonko S. A., Nattier B. A., Mohan R. S., Tetrahedron Lett., 40,
7657—7659 (1999).
2
2
2
2
1
products were identified by comparing their melting points, TLC, H-NMR
and MS spectra with those of the authentic samples. 3a: Yellow prisms 25) Chang S., Lee M., Ko S., Lee P. H., Synth. Commun., 32, 1279—1284
4
4)
(
from hexane–CH Cl ), mp 94—95 °C (lit. 94—95 °C), 3b: Yellow nee-
(2002).
2
2
45)
dles (from hexane–CH Cl ), mp 167—168 °C (lit. 168—169 °C), 3c: Yel- 26) Rao T. V., Dongre R. S., Jain S. L., Sain B., Synth. Commun., 32,
low needles (from hexane–CH Cl ), mp 83—84 °C (lit. 84—85 °C), 3d:
Yellow needles (from CHCl ), mp 155—156 °C (lit. 155—156 °C), 3e: 27) Iwase S., Morita K., Tajima K., Fakhruddin A., Nishiyama H., Chem.
Yellow prisms (from hexane–CH Cl ), mp 102—104 °C (lit.
03 °C), 3f: Yellow needles (from hexane–CH Cl ), mp 131—133 °C (lit.
31—132 °C), 3g: Yellow needles (from CHCl ), mp 225—226 °C (lit.
2
2
45)
2637—2641 (2002).
2
2
45)
3
44)
102—
Lett., 2002, 284—285 (2002).
28) Shvo Y., Goldman-Lev V., J. Organomet. Chem., 650, 151—156
(2002).
2
2
4
4)
4)
1
1
2
2
2
4
3
26 °C).
29) Huang Y., Shen Y., Chen C., Synthesis, 1985, 651—652 (1985).
30) Akiba K.-y., Ohnari H., Ohkata K., Chem. Lett., 1985, 1577—1580
Acknowledgements The present work was financially supported by
(1985).
Takeda Science Foundation and a Grant-in-Aid for Scientific Research (C) 31) Ohkata K., Ohnari H., Akiba K.-y., Nippon Kagaku Kaishi, 1987,
from Japan Society for the Promotion of Science (JSPS). The authors also
thank the Specific Research Fund from Hokuriku University for generous fi-
nancial support.
1267—1273 (1987).
32) Nomura R., Takebe A., Matsuda H., Chem. Express, 1, 375—378
(1986).
3
3) It is well known that triarylstibane oxides (Ar SbO) including Ar Sb-
3
3
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