Display Settings:

Format

Send to:

Choose Destination
See comment in PubMed Commons below
J Org Chem. 2009 Oct 16;74(20):7822-33. doi: 10.1021/jo901525u.

Mechanism of the Ni(0)-catalyzed vinylcyclopropane-cyclopentene rearrangement.

Author information

  • 1Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, USA.

Abstract

A combination of physical organic experiments and quantum chemical calculations were used to construct a detailed mechanistic model for the Ni(0)-N-heterocyclic carbene-catalyzed vinylcyclopropane-cyclopentene rearrangement that involves a mutistep oxidative addition/haptotropic shift/reductive elimination pathway. No evidence for the intermediacy of radicals or zwitterions was found. The roles of substituents on the vinylcyclopropane substrate and variations in the ligands on Ni were evaluated. It is postulated that bulky carbene ligands facilitate formation of the active catalyst species.

PMID:
19780523
[PubMed - indexed for MEDLINE]
PMCID:
PMC2762793
Free PMC Article
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Icon for American Chemical Society Icon for PubMed Central
    Loading ...
    Write to the Help Desk