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

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

Volume: 14 Issue: 2

Author(s): David E. Lewis*

Affiliation:

• Department of Chemistry, University of Wisconsin-Eau Claire, P.O. Box: 4004, Eau Claire, WI 54702- 4004,United States

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

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.

Cite this article as:

Lewis E. David*, Intramolecular Pericyclic Reactions of Acetylene Derivatives Leading to Dehydroaromatic and Related Species, Mini-Reviews in Organic Chemistry 2017; 14 (2) . https://dx.doi.org/10.2174/1570193X14666170206144743