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

• Main Authors: Marković Zoran, Šolaja Bogdan, Milić Dragan, Juranić Ivan, Gašić Miroslav J.
• Format: Article
• Language: English
• Published: Serbian Chemical Society 2000-01-01
• Series: Journal of the Serbian Chemical Society
• Subjects: steroids; phenols; quinols; epoxyquinols; oxidation mndo-pm3 study
• Online Access: http://www.doiserbia.nb.rs/img/doi/0352-5139/2000/0352-51390007491M.pdf
• ISSN: 0352-5139; 1820-7421

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.