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Issue 2, 2008
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Reactions in the conjugated ‘ene–ene–yne’ manifold: five-membered ring fragmentation and ring formation via coarctate/pseudocoarctate mechanisms

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Abstract

The fragmentation of a 5-membered heteroaromatic ring to afford a conjugated ene–ene–yne skeleton, and the corresponding reverse process, cyclization of the hetero-ene–ene–yne motif to generate a variety of heterocyclic systems, are the subject of this review. These synthetically useful reactions, which proceed through a coarctate/pseudocoarctate mechanistic pathway, are unique in that they involve the generation of either a carbene or nitrene intermediate, and provide access to hard to obtain heterocyclic or ene–ene–yne structures. While fragmentation of heteroaromatic rings containing a exocyclic carbene or nitrene has been well documented in the literature for over 40 years, the use of hetero-ene–ene–yne precursors to synthesize heterocycles is a relatively new approach that is generating much interest in the literature. This review highlights both the synthetic and mechanistic aspects of these unique reactions.

Graphical abstract: Reactions in the conjugated ‘ene–ene–yne’ manifold: five-membered ring fragmentation and ring formation via coarctate/pseudocoarctate mechanisms

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Article information


Submitted
12 Jul 2007
First published
06 Sep 2007

Chem. Soc. Rev., 2008,37, 343-364
Article type
Critical Review

Reactions in the conjugated ‘ene–ene–yne’ manifold: five-membered ring fragmentation and ring formation via coarctate/pseudocoarctate mechanisms

L. D. Shirtcliff, S. P. McClintock and M. M. Haley, Chem. Soc. Rev., 2008, 37, 343
DOI: 10.1039/B705457M

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