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

[ Vol. 14 , Issue. 2 ]


David E. Lewis*   Pages 107 - 121 ( 15 )


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.


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


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

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