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Letter

Computational Study and Analysis of the Kinetic Isotope Effects of the Rearrangement of cis-Bicyclo[4.2.0]oct-7-ene to cis,cis-Cycloocta-1,3-diene

Supporting Info

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

Departamento de Qumica Orgnica, Facultade de Qumica, Universidade de Vigo, Lagoas-Marcosende, E-36310, Vigo, Galicia, Spain

Org. Lett., 2006, 8 (10), pp 2055–2058

DOI: 10.1021/ol060465f

Publication Date (Web): April 21, 2006

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

On the basis of KIE experiments, the ring opening of cis-bicyclo[4.2.0.]oct-7-ene has been suggested as an anti-Woodward−Hoffmann reaction candidate. We hereby report the results of a high-level computational study of the alternate reaction pathways which proves that the energy profiles show a clear preference for the conrotatory (W−H allowed) ring opening followed by double-bond isomerization. Computed KIE values for the aforementioned mechanism are in good agreement with the experimental values.

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