Acylation du (cyclopropylméthyl) triméthylsilane. Une nouvelle voie d'accès aux énones non conjuguées

M Grignon-Dubois, J Dunogues…

Index: Grignon-Dubois, M.; Dunogues, J.; Calas, R. Canadian Journal of Chemistry, 1981 , vol. 59, p. 802 - 806

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Citation Number: 12

Abstract

Acylation of (cyclopropylmethyl) trimethylsilane using RCOCl/AlCl3 (R: saturated hydrocarbon group) constitutes a mild, convenient route to β, γ-unsaturated ketones free from the conjugated isomers. With α, β-unsaturated acyl chlorides a competitive reaction between the CH and C-Si allylic cleavage is observed whereas chloroacetyl chloride affords the γ, δ-ethylenic corresponding ketone. A mechanism involving the catalytic role of HCl in ...