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.
[reaction: see text] 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.
López
Carlos Silva
CS
Departamento de Química Organica, Facultade de Química, Universidade de Vigo, Lagoas-Marcosende, Galicia, Spain.
Faza
Olalla Nieto
ON
de Lera
Angel R
AR