GENERATION OF THE ALPHA-SULFINYL CARBENOID FROM ALPHA-CHLORO SULFOXIDES - A NEW METHOD FOR ONE-CARBON HOMOLOGATION OF KETONES TO ALPHA-SULFINYL KETONES

被引：16

作者：

SATOH, T ^{[1
]}

HAYASHI, Y ^{[1
]}

MIZU, Y ^{[1
]}

YAMAKAWA, K ^{[1
]}

机构：

[1] SCI UNIV TOKYO, FAC PHARMACEUT SCI, ICHIGAYA FUNAGAWARA MACHI, SHINJUKU KU, TOKYO 162, JAPAN

来源：

BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN | 1994年 / 67卷 / 05期

关键词：

D O I：

10.1246/bcsj.67.1412

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Treatment of 1-chloroalkyl phenyl sulfoxides with a base gave carbenoids rather than free carbenes. The carbenoids were successfully used in a new method for homologation of ketones to alpha-sulfinyl ketones. Treatment of the carbanion of chloromethyl phenyl sulfoxide with ketones gave the adducts, alpha-chloro beta-hydroxy sulfoxides, in nearly quantitative yields. The adducts were treated with excess lithium diisopropylamide to give one-carbon homologated alpha-sulfinyl ketones via alpha-sulfinyl beta-oxido carbenoids in moderate to good yields. This type of reaction was found not to occur with the corresponding sulfones.

引用

页码：1412 / 1418

页数：7

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