Electrochemical Oxidation of 4-Methylcatechol in the Presence of β-Diketones

Electrochemical oxidation of 4-methylcatechol (1) in the presence of, benzoylacetone (2), dibenzoylmethane (3), 3-hydroxy-1H-phenalen-1-one (4), acetylacetone (5), dimedone (6), and 2-acetylcyclohexanone (7) as nucleophiles has been studied in detail by cyclic voltammetry and controlled-potential coulometry. The results indicate that the electrochemically generated quinone participates in Michael addition reaction with 2–7 via various mechanisms to produce new organic compounds. Furthermore, our studies show that the structure of intermediates play a crucial role in product selectivity under controlled-potential conditions. Various types of products were also obtained through the selective oxidation at the surface of a carbon electrode in an undivided cell.