Electrochemical oxidation of catechols in the presence of cyanoacetone and methyl cyanoacetate

Electrochemical oxidation of catechols is studied in the presence of cyanoacetone and methyl cyanoacetate as nucleophiles in aqueous solutions by means of cyclic voltammetry and controlled-potential coulometry. The reaction mechanism is believed to be ECEC including oxidation of catechol, intermolecular Michael addition, oxidation of adduct and intramolecular Michael addition. Final products are nitrile containing benzofurans. The observed homogeneous rate constants (kobs) of reactions are estimated by digital simulation of cyclic voltammograms. Also the effects of nucleophile and catechol structures on the rate constants of chemical reactions are described.