Acylation du (cyclopropylméthyl)triméthylsilane. Une nouvelle voie d'accès aux énones non conjuguées
Keyword(s):
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.
Keyword(s):
Keyword(s):
1993 ◽
Vol 268
(32)
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pp. 24149-24155
1989 ◽
Vol 264
(32)
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pp. 19132-19137
1990 ◽
Vol 31
(51)
◽
pp. 7457-7460
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1977 ◽
Vol 82
(25)
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pp. 3634-3642
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