title: Preparation of Vinylcyclopropanes by Sodium Mediated Reductive Isomerization of Methylenecyclopropanes.
abstract: We disclosed therein a new reaction of reductive isomerization of methylenecyclopropanes (MCPs) to vinylcyclopropanes (VCPs). On treatment with sodium metal in liquid ammonia, MCPs bearing a C-O bond at allylic position undergo both a reductive cleavage of the C-O bond and an isomerization of the C-C double bond giving rise to VCPs. The scope of the reductive isomerization was investigated and showed a broad applicability since various functional groups are tolerated. MCP substrates were straightforwardly prepared by a palladium-promoted [2 + 1] cycloaddition between norbornene derivatives with alkynes.
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313 , 13397 Marseille, France.
authors.forename: Karel
authors.initials: K
authors.lastname: Le Jeune
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313 , 13397 Marseille, France.
authors.forename: Sabine
authors.initials: S
authors.lastname: Chevallier-Michaud
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313 , 13397 Marseille, France.
authors.forename: David
authors.initials: D
authors.lastname: Gatineau
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313 , 13397 Marseille, France.
authors.forename: Laurent
authors.initials: L
authors.lastname: Giordano
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313 , 13397 Marseille, France.
authors.forename: Alphonse
authors.initials: A
authors.lastname: Tenaglia
authors.affiliation: Aix Marseille Université, Centrale Marseille, CNRS, iSm2 UMR 7313 , 13397 Marseille, France.
authors.forename: Hervé
authors.initials: H
authors.lastname: Clavier