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

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

Acylation of (cyclopropylmethyl)trimethylsilane using RCOCl/AlCl 3 (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 CSi allylic cleavage is...

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Veröffentlicht in:Canadian journal of chemistry 1981-03, Vol.59 (5), p.802-806
Hauptverfasser: Grignon-Dubois, M, Dunoguès, J, Calas, R
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container_title Canadian journal of chemistry
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creator Grignon-Dubois, M
Dunoguès, J
Calas, R
description Acylation of (cyclopropylmethyl)trimethylsilane using RCOCl/AlCl 3 (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 CSi 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.
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title Acylation du (cyclopropylméthyl)triméthylsilane. Une nouvelle voie d'accès aux énones non conjuguées
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