SINGLET OXYGEN ADDITIONS TO O[10.2.1.0(2,11).0(4,9).0(4,14).0(9,13)]PENTADECA, 5,7-DIEN-3,10-DIONES - A REMARKABLE SUBSTITUENT EFFECT ON PI-FACE SELECTIVITY INDUCED BY TRANSITION-STATE GEOMETRIC DISTORTIONS
G. Mehta et al., SINGLET OXYGEN ADDITIONS TO O[10.2.1.0(2,11).0(4,9).0(4,14).0(9,13)]PENTADECA, 5,7-DIEN-3,10-DIONES - A REMARKABLE SUBSTITUENT EFFECT ON PI-FACE SELECTIVITY INDUCED BY TRANSITION-STATE GEOMETRIC DISTORTIONS, Journal of the Chemical Society, Chemical Communications, (6), 1995, pp. 677-678
Face selectivity in singlet oxygen addition to a rigid polycyclic dien
e is reversed by sterically neutral 1,4-substitution, an effect attrib
uted to lone pair repulsions induced by out-of-plane bending at the tr
ansition state.