Bulletin of the Chemical Society of Japan p. 1412 - 1418 (1994)
Update date:2022-09-26
Topics:
Satoh, Tsuyoshi
Hayashi, Yasumasa
Mizu, Yasuhiro
Yamakawa, Koji
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 α-sulfinyl ketones.Treatment of the carbanion of chloromethyl phenyl sulfoxide with ketones gave the adducts, α-chloro β-hydroxy sulfoxides, in nearly quantitative yields. the adducts were treated with excess lithium diisopropylamide to give one-carbon homologated α-sulfinyl ketones via α-sulfinyl β-oxido carbenoids in moderate to good yields.This type of reaction was found not to occur with the corresponding sulfones.
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