Electrooxidative pinacol-type rearrangement of beta-hydroxy sulfides. Efficient C-S cleavage mediated by chloride ion oxidation

被引：12

作者：

Kimura, M ^{[1
]}

Kobayashi, K ^{[1
]}

Yamamoto, Y ^{[1
]}

Sawaki, Y ^{[1
]}

机构：

[1] NAGOYA UNIV,FAC ENGN,DEPT APPL CHEM,NAGOYA,AICHI 46401,JAPAN

来源：

TETRAHEDRON | 1996年 / 52卷 / 12期

关键词：

D O I：

10.1016/0040-4020(96)00130-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrooxidation of alpha-phenyl substituted beta-hydroxy sulfides in dichloromethane in the presence of chloride ions as the electrolyte results in a novel pinacol-type rearrangement to give 2-phenyl substituted ketones like 2-phenylcycloalkanone as the ring expansion product. The rearrangement is induced by an electrogenerated chloronium ion, which effects, instead of common C-C scission, a selective C-S cleavage of beta-hydroxy sulfides.

引用

页码：4303 / 4310

页数：8

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