Conrotatory ring-opening reactions of cyclopropyl anions in monocyclic and tricyclic systems.
[reaction: see text] 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.
Faza
Olalla Nieto
ON
Departamento de Química Orgánica, Facultad de Química, Universidad de Vigo, Lagoas-Marcosende s/n, 36200 Vigo, Spain.
López
Carlos Silva
CS
Alvarez
Rosana
R
de Lera
Angel R
AR