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Mini-Reviews in Organic Chemistry


ISSN (Print): 1570-193X
ISSN (Online): 1875-6298

Review Article

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

Author(s): David E. Lewis*

Volume 14, Issue 2, 2017

Page: [107 - 121] Pages: 15

DOI: 10.2174/1570193X14666170206144743

Price: $65


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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