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The Woodward-Hoffmann-De Puy rule revisited
Olalla Nieto Faza1, Carlos Silva López, Rosana Alvarez
1Departamento de Química Orgánica, Facultade de Química, Universidade de Vigo, Lagoas-Marcosende s/n, 36200 Vigo, Spain.
Organic Letters
|March 12, 2004
Abstract:
[structure: see text] An estimate of the kinetic advantage, in the gas phase and in MeOH, of one of the two allowed disrotatory movements in the electrocyclic ring opening of cyclopropyl derivatives has been theoretically obtained at the B3LYP/6-311++G level. Confirming the Woodward-Hoffmann-DePuy rule, the torquoselectivity of this process is attributed to charge donation from the dissociating C-C bond to the antibonding orbital of the breaking C-Br bond. Substituents do not modify the inherent torquoselectivity.