Generation of the α-Sulfinyl Carbenoid from α-Chloro Sulfoxides: A New Method for One-Carbon Homologation of Ketones to α-Sulfinyl Ketones
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.
Satoh, Tsuyoshi,Hayashi, Yasumasa,Mizu, Yasuhiro,Yamakawa, Koji
p. 1412 - 1418
(2007/10/02)
α-Sulfinyl carbenoid: One-carbon homologation of ketones to α-sulfinyl ketones using chloromethyl phenyl sulfoxide
Addition of the carbanion of chloromethyl phenyl sulfoxide to ketones gave the adducts, which were treated with lithium diisopropylamide to afford one-carbon homologated α-sulfinyl ketones via α-sulfinyl carbenoids in moderate to high yields.
Satoh, Tsuyoshi,Hayashi, Yasumasa,Mizu, Yasuhiro,Yamakawa, Koji
p. 7181 - 7184
(2007/10/02)
Chemoselective Method for the Preparation of Phenyl Sulfoxides by the Oxidation of Phenyl Sulfides with 2-Hydroperoxy-2-methoxypropane
Phenyl sulfoxides are easily prepared by the chemoselective oxidation of the corresponding sulfides with molecular equivalents of 2-hydroperoxy-2-methoxypropane.This reagent is generated from 2,3-dimethyl-2-butene by ozonization in methanol.
Leriverend, Pierre,Leriverend, Marie-Louise
p. 587 - 588
(2007/10/02)
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