Jump to main content
Jump to site search

Issue 2, 2014
Previous Article Next Article

Distortion-accelerated cycloadditions and strain-release-promoted cycloreversions in the organocatalytic carbonyl-olefin metathesis

Author affiliations

Abstract

The mechanism of hydrazine-catalyzed carbonyl-olefin metathesis relying on a novel (3 + 2) strategy is studied by density functional theory (DFT) calculations. The origins of the special reactivity of cyclopropene in this transformation are revealed, and the reactivities of different alkenes in the (3 + 2) cycloadditions and cycloreversions are compared. It is found that the ease of distortion of reactants accelerates cycloadditions, and that the strain release is the controlling factor for cycloreversions.

Graphical abstract: Distortion-accelerated cycloadditions and strain-release-promoted cycloreversions in the organocatalytic carbonyl-olefin metathesis

Back to tab navigation

Supplementary files

Publication details

The article was received on 17 Oct 2013, accepted on 01 Nov 2013 and first published on 04 Nov 2013


Article type: Edge Article
DOI: 10.1039/C3SC52882K
Citation: Chem. Sci., 2014,5, 471-475
  •   Request permissions

    Distortion-accelerated cycloadditions and strain-release-promoted cycloreversions in the organocatalytic carbonyl-olefin metathesis

    X. Hong, Y. Liang, A. K. Griffith, T. H. Lambert and K. N. Houk, Chem. Sci., 2014, 5, 471
    DOI: 10.1039/C3SC52882K

Search articles by author

Spotlight

Advertisements