RACEMIZATION OF SULFINIC ESTERS WITH TRICHLOROACETIC ANHYDRIDE

被引：14

作者：

DRABOWICZ, J ^{[1
]}

OAE, S ^{[1
]}

机构：

[1] UNIV TSUKUBA,DEPT CHEM,SAKURA,IBARAKI 300-31,JAPAN

来源：

TETRAHEDRON | 1978年 / 34卷 / 01期

关键词：

D O I：

10.1016/0040-4020(78)88037-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Both alkane- and arene-sulfinates undergo racemization and oxygen exchange reaction with trich-loroacetic anhydride. The rate of racemization of (-)menthyl (-)p-toluenesulfinate was found to be twice that of oxygen exchange, suggesting the reaction involves a Walden inversion. When reaction was carried out in benzene, the rate of racemization was found to be first order with respect to both sulfinic ester and trichloroacetic anhydride. The substituent effect is large (p = -1.53) suggesting that the initial acylation is the rate-determining step. The rate of racemization was found to be retarded by the addition of perhaloacetic acid while very small catalytic effect of mercuric chloride was observed. © 1978.

引用

页码：63 / 66

页数：4

共 21 条

[1]

ANDERSEN KK, 1962, TETRAHEDRON LETT, P93

[2]

ANDERSEN KK, 1971, INT J SULFUR CHEM B, V6, P69

[3] THERMAL RACEMIZATION OF ALLYLIC SULFOXIDES AND INTERCONVERSION OF ALLYLIC SULFOXIDES AND SULFENATES - MECHANISM AND STEREOCHEMISTRY [J].