Investigation of Electrochemically Induced Michael Addition Reactions of Ortho- and Para-banzoquinones with 2-Mercaptobenzimidazole: Application to Electrosynthesis
Davood Nematollahi, Saied S.H. Davarani, Pari Mirahmadpour and Fahimeh Varmaghani
Affiliation: Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran, 65178-38683.
Electrochemical oxidation of hydroquinone and catechol derivatives (1a-1d) has been studied in the presence
of 2-mercaptobenzimidazole (3) as a nucleophile in water/acetonitrile (85/15, v/v) solutions using cyclic voltammetry.
Our results indicate that electrogenerated benzoquinone participated in a Michael addition reaction with 2-
mercaptobenzimidazole (3) and via an EC mechanism were converted to the corresponding thioimidazole compounds.
These products were obtained in good yields using a carbon electrode in an undivided cell.
Keywords: Catechol, Hydroquinone, Electrochemical synthesis, Thioimidazole, Cyclic voltammetry, Michael addition
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