Molecular orbital study of the oxidation of steroidal phenols into quinols and epoxyquinols

The MO study showed that the radical oxidation of phenols into quinols occurs readily. Further radical oxidation (in the m-CPBA/(BzO)2/hv system) of quinols occurs through appropriate biradical species with an activation energy of 79.5 kJ/mol yielding syn-epoxyquinols. The stereochemical outcome presented in this study is in full agreement with the experimental results.