Abstract
The chiral-optical effects of heteroannular cisoid dienes are attributed to the dissymmetry of the skewed diene chromophore as in the case of homoannular cisoid dienes and of transoid dienes. The sign of these effects for a small number of heteroannular cisoid dienes is opposite to that predicted from the “diene rule” (1). This inversion of sign is ascribed to the change in electronic properties of the diene when, as in these compounds, the dihedral angle about the central bond is very large compared to that of the homoannular dienes. Consistent with these observations, recent theoretical treatments of the functional dependence of the rotatory strengths on the dihedral angle demonstrate that the sign of the CD and ORD effects can change at large angles.
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