Electrochemical oxidation of 4-methylcatechol in the presence of β-diketones

Article abstract of DOI:10.1246/bcsj.81.1505

Electrochemical oxidation of 4-methylcatechol (1) in the presence of, benzoylacetone (2), dibenzoylmethane (3), 3-hydroxy-1H-phenalen-l-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 electro-chemically 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.