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

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02278877
Contributor : Sylvain Oudeyer <>
Submitted on : Wednesday, September 4, 2019 - 5:01:41 PM
Last modification on : Wednesday, April 15, 2020 - 9:06:02 AM

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Sylvain Oudeyer, Eric Leonel, Jean Paul Paugam, Jean-Yves Nédélec. Copper-catalyzed electrosynthesis of 1-acyl-2,2-diphenylcyclopropanes and their behaviour in acidic medium. Tetrahedron, Elsevier, 2003, 59 (7), pp.1073-1081. ⟨10.1016/S0040-4020(02)01620-4⟩. ⟨hal-02278877⟩

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