" Syn-Effect" in the Conversion of (E)-Vinylic Sulfones to the Corresponding Allylic Sulfones.

…, Y Sasada, T Ohtani, T Asada, H Kinoshita…

Index: Hirata, Takaki; Sasada, Yoshihiro; Ohtani, Takashi; Asada, Takahiro; Kinoshita, Hideki; et al. Bulletin of the Chemical Society of Japan, 1992 , vol. 65, # 1 p. 75 - 96

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Citation Number: 40

Abstract

It was found that (E)-vinylic sulfones preferentially afford (Z)-allylic sulfones as kinetically- controlled products by treatment with a base under mild conditions, while (Z)-vinylic sulfones give (E)-allylic sulfones. Such stereochemical relationship was rationalized by “syn-effect”, and its relative degree for various substituents was determined by observation of E/Z ratios of the allylic sulfones resulted from the corresponding γ-mono-or γ, γ-disubstituted vinylic ...