Intramolecular Pericyclic Reactions of Acetylene Derivatives Leading to Dehydroaromatic and Related Species

Author(s): David E. Lewis*.

Journal Name: Mini-Reviews in Organic Chemistry

Volume 14 , Issue 2 , 2017

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Graphical Abstract:


Alkynes and cumulenes share the common feature of at least one sp-hybridized carbon atom in the molecule. This leads to the molecules having relatively high energy in the thermodynamic sense, but also having high stability in the kinetic sense. Enediynes, enyne-cumulenes and yne-diynes all undergo pericyclic reactions resulting in cycloaromatization to dehydrobenzenes and related products. In this review, the history, mechanism and synthetic uses of these reactions are discussed.

Keywords: Bergman cyclization, Schreiner-Pascal cyclization, Myers-Saito cyclization, Schmittel cyclization, Garratt- Braverman cyclization, dehydro-Diels-Alder reactions, cycloaromatization.

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Article Details

Year: 2017
Page: [107 - 121]
Pages: 15
DOI: 10.2174/1570193X14666170206144743
Price: $65

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