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Letter

Conrotatory Ring-Opening Reactions of Cyclopropyl Anions in Monocyclic and Tricyclic Systems

Olalla Nieto Faza, Carlos Silva López, Rosana Álvarez, and Ángel R. de Lera*

Departamento de Qumica Orgnica, Facultad de Qumica, Universidad de Vigo, Lagoas-Marcosende s/n, 36200 Vigo, Spain

Org. Lett., 2004, 6 (6), pp 901–904

DOI: 10.1021/ol036448x

Publication Date (Web): February 19, 2004

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, qolera@uvigo.es

Abstract

Only conrotatory transition structures were located by B3LYP6-311++G(3df, 2p) computations for the electrocyclic ring opening of cyclopropyl anions having different substituents (H, Me, CN). The transition structure for the similarly substituted cyclopropyl anion fused to a bicyclic system exhibits the same features, in apparent contradiction with the observed product. A reaction path where the direction of twist changes after the transition state provides an explanation alternative to those proposed in recent reports.

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