Bulletin of the Chemical Society of Japan
Online ISSN : 1348-0634
Print ISSN : 0009-2673
ISSN-L : 0009-2673
Reaction of α-Chloro Sulfoxides with Carbonyl and Thiocarbonyl Compounds
Gen-ichi TsuchihashiKatsuyuki Ogura
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1972 Volume 45 Issue 7 Pages 2023-2027

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Abstract

Ghloromethyl methyl sulfoxide undergoes a Darzens-type reaction with carbonyl compounds in the presence of potassium t-butoxide in t-butanol to afford methylsulfinyloxirane derivatives. The stereochemistry of this reaction has been studied. The reaction with a symmetrical ketone appeared to proceed stereospecifically to give only one isomer. On the other hand, the reaction with unsymmetrical ketones such as pinacolone or acetophenone produced a mixture of two diastereoisomers, in which a thermodynamically unstable isomer was predominant. The reaction with thiobenzophenone gave 1,1-diphenyl-2-methylsulfinylethylene which seems to have been formed from the intermediacy of 2,2-diphenyl-3-methylsulfinylthiirane. Mechanisms of these reactions are also discussed.

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