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Issue 4, 2009
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Sigmatropic rearrangements of ‘onium’ ylids

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Rearrangement reactions occupy a special place within the canon of organic synthesis, by virtue of the inherently high efficiency of chemical processes which form and break bonds by redistribution of electrons around a retained atomic framework. Within the broader class, sigmatropic rearrangements are chemical processes defined by mechanisms involving unimolecular migration of σ-bonds with concomitant redistribution of one or more π-bonds. Sigmatropic processes may involve uncharged or charged species, with the charges located on carbon or heteroatoms; the latter reaction type is the subject of this tutorial review.

Graphical abstract: Sigmatropic rearrangements of ‘onium’ ylids

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The article was received on 28 Apr 2008 and first published on 05 Mar 2009

Article type: Tutorial Review
DOI: 10.1039/B604828P
Citation: Chem. Soc. Rev., 2009,38, 1027-1038
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    Sigmatropic rearrangements of ‘onium’ ylids

    J. B. Sweeney, Chem. Soc. Rev., 2009, 38, 1027
    DOI: 10.1039/B604828P

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