Stereochemistry of the Removal of Sulfur from Episulfides by the Action of Phenyllithium and Triethyl Phosphite

NP Neureiter, FG Bordwell

Index: Neureiter; Bordwell Journal of the American Chemical Society, 1959 , vol. 81, p. 578

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Citation Number: 79

Abstract

The reaction of episulfides with phenyllithium has been shown to result in the abstraction of sulfur to give lithium thiophenoxide and the corresponding olefin, presumably by nucleophilic attack of the incipient phenyl carbanion on sulfur.'Our interest in the stereochemistry of this reaction was aroused, first by the observation that cis-2-butene is the major product obtained on treating a-chloroethyl ethyl sulfone with alkali2 (an olefin- ...