The Woodward-Hoffmann-De Puy rule revisited. Faza, O., López, C., Álvarez, R., & De Lera, Á. Organic Letters, 6(6):905-908, 2004.
doi  abstract   bibtex   
(Equation presented) 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.
@ARTICLE{Faza2004905,
author={Faza, O.N. and López, C.S. and Álvarez, R. and De Lera, Á.R.},
title={The Woodward-Hoffmann-De Puy rule revisited},
journal={Organic Letters},
year={2004},
volume={6},
number={6},
pages={905-908},
doi={10.1021/ol036449p},
abstract={(Equation presented) 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.},
}

Downloads: 0