1606-37-7Relevant academic research and scientific papers
Acylation du (cyclopropylmethyl)trimethylsilane. Une nouvelle voie d'acces aux enones non conjuguees
Grignon-Dubois, M.,Dunogues, J.,Calas, R.
, p. 802 - 806 (2007/10/02)
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 C-H 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 the formation of β,γ-unsaturated and chloroketones is proposed.
