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Issue 76, 2012
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Coarctate cyclization reactions: a primer

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Abstract

The cleavage of five-membered heterocycles possessing an exocyclic carbene or nitrene to form conjugated ene–ene–yne systems has been documented for over 40 years; however, the reverse reaction, using a conjugated “ene–ene–yne” precursor to form a heterocycle is a relatively new approach. Over the past decade, the Haley and Herges groups have studied computationally and experimentally the cyclization of the “hetero-ene–ene–yne” motif via an unusual class of concerted reactions known as coarctate reactions. This feature article details our synthetic and mechanistic work involving triazene–arenealkynes and structurally-related systems to generate heterocycles using coarctate chemistry.

Graphical abstract: Coarctate cyclization reactions: a primer

  • This article is part of the themed collection: Aromaticity
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Publication details

The article was received on 05 Jun 2012, accepted on 16 Jul 2012 and first published on 31 Jul 2012


Article type: Feature Article
DOI: 10.1039/C2CC34026G
Citation: Chem. Commun., 2012,48, 9441-9455

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    Coarctate cyclization reactions: a primer

    B. S. Young, R. Herges and M. M. Haley, Chem. Commun., 2012, 48, 9441
    DOI: 10.1039/C2CC34026G

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