Polyfunctional tetrazolic thioethers through electrooxidative/Michael-type sequential reactions of 1,2- and 1,4-dihydroxybenzenes with 1-phenyl-5-mercaptotetrazole

In the presence of 1-phenyl-5-mercaptotetrazole as a nucleophile, electrochemical oxidations of 1,2- and 1,4-dihydroxybenzenes have been investigated in aqueous solution using cyclic voltammetry and controlled-potential coulometry. The voltammetric results indicate that an electrooxidative/Michael-type sequential reaction occurs between the mercaptide anion and the electrochemically generated benzoquinones leading to the corresponding polyfunctional tetrazolic thioethers. The mechanism of electrochemical reaction is proved as an EC pathway using controlled-potential coulometry. In addition, the electrosyntheses of tetrazolic thioethers have been successfully performed in ambient conditions in an undivided cell using an environmentally friendly method with high atom economy.