Optical activity in βγ-unsaturated ketones. Part 1. Effect of the direction of the electric transition dipole moment in the aromatic group in benzobicyclo[2.2.2]octen-2-one derivatives

Abstract

In methoxybenzobicyclo[2.2.2]octen-2-one derivatives, a change in the position of the methoxy-group brings about a change in the direction of the transition dipole moment without much alteration in the σ-electron distribution. We have studied the effects of the change of the direction of the local chromophore on the optical activity and analysed these by application of dynamic and static coupling mechanisms. We have concluded that the optical activity is mainly produced by [graphic omitted]–[graphic omitted] coupling and depends on the direction of the local transition moments.