Synthetic methods and reactions. 146. Olefins from crowded carbonyl compounds with tert-butyllithium (tert-butylmagnesium chloride)/thionyl chloride. Study of …

…, AH Wu, O Farooq, GKS Prakash

Index: Olah, George A.; Wu, An-hsiang; Farooq, Omar; Prakash, G. K. Surya Journal of Organic Chemistry, 1990 , vol. 55, # 6 p. 1792 - 1796

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Abstract

Crowded carbonyl compounds when reacted with tert-butyllithium or tert-butylmagnesium chloride followed by thionyl chloride treatment give in a one-pot reaction olefins in good to excellent yields. In the case of highly crowded tertiary systems the reaction occurs either by rearrangement followed by the loss of a tert-butyl group (as isobutylene) or rearrangement accompanied by deprotonation, indicating the carbocationic nature of the process. The ...