The Journal of Organic Chemistry

Synthetic methods and reactions. 140. One-pot preparation of crowded olefins from hindered ketones with alkyllithiums and thionyl chloride

GA Olah, AH Wu, O Farooq

Index: Olah, George A.; Wu, An-hsiang; Farooq, Omar Journal of Organic Chemistry, 1989 , vol. 54, # 6 p. 1375 - 1378

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Citation Number: 16

Abstract

A series of crowded olefins were prepared in high yield by the one-pot reaction of in situ generated lithium alkoxides, formed from hindered ketones and alkyllithiums, with thionyl chloride. The prepared olefm are generally inaccessible by either the Wittig reaction or using Grignard reagents because of predominant electron-transfer reduction of the hindered ketones.