Preparation of Vinylcyclopropanes by Sodium Mediated Reductive Isomerization of Methylenecyclopropanes | Zendy

Karel Le Jeune | Zendy; Sabine ChevallierMichaud | Zendy; David Gatineau | Zendy; Laurent Giordano | Zendy; Alphonse Tenaglia | Zendy; Hervé Clavier | Zendy

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Preparation of Vinylcyclopropanes by Sodium Mediated Reductive Isomerization of Methylenecyclopropanes

Author(s) -

Karel Le Jeune,

Sabine ChevallierMichaud,

David Gatineau,

Laurent Giordano,

Alphonse Tenaglia,

Hervé Clavier

Publication year - 2015

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.5b01205

Subject(s) - isomerization , chemistry , cycloaddition , allylic rearrangement , double bond , medicinal chemistry , reductive elimination , bond cleavage , photochemistry , organic chemistry , catalysis

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.

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