Delocalization and stability of o- and p-quinone methides: A HMO study

Abstract

A series of twenty one p- and o-quinone methides has been investigated by the HMO method. Stability predictions for compounds I-XIII are based on a combination of their topological resonance energy, nucleophilic reactivity and dimerization ability. The obtained results have been verified by the synthesis of four new quinone methides IIb, Vb, VIa and VIb.