Copper-catalyzed electrosynthesis of 1-acyl-2,2-diphenylcyclopropanes and their behaviour in acidic medium

The formation of 1-acyl-2,2-diphenylcyclopropanes is performed under mild electrochemical conditions. These cyclopropane derivatives, through acid-catalyzed ring-opening, lead to γ,γ-diphenyl-β,γ-unsaturated carbonyl compounds which evolve into either substituted naphthalenes, or β-benzhydryl-α,β-cy...

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Bibliographic Details
Published in:Tetrahedron 2003-02, Vol.59 (7), p.1073-1081
Main Authors: Oudeyer, Sylvain, Léonel, Eric, Paugam, Jean Paul, Nédélec, Jean-Yves
Format: Article
Language:English
Subjects:
acyl cyclopropanes
benzannulation
Catalysis
Chemical Sciences
electro-organic synthesis
Organic chemistry
substituted naphthalenes
β-benzhydryl-α,β-cycloalkenones
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Summary:The formation of 1-acyl-2,2-diphenylcyclopropanes is performed under mild electrochemical conditions. These cyclopropane derivatives, through acid-catalyzed ring-opening, lead to γ,γ-diphenyl-β,γ-unsaturated carbonyl compounds which evolve into either substituted naphthalenes, or β-benzhydryl-α,β-cycloalkenones depending on the acyclic or cyclic nature of the intermediate allyl ketone. 1-Acyl-2,2-diphenylcyclopropanes prepared under mild electrochemical conditions, are converted, in acidic medium, first into γ,γ-diphenyl-β,γ-unsaturated ketones and subsequently into substituted naphthalenes or β-benzhydryl-α,β-cycloalkenones.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)01620-4