Investigation of Electrochemically Induced Michael Addition Reactions of Ortho- and Para-banzoquinones with 2-Mercaptobenzimidazole: Application to Electrosynthesis

Title:Investigation of Electrochemically Induced Michael Addition Reactions of Ortho- and Para-banzoquinones with 2-Mercaptobenzimidazole: Application to Electrosynthesis

Volume: 11 Issue: 6

Author(s): Davood Nematollahi, Saied S.H. Davarani, Pari Mirahmadpour and Fahimeh Varmaghani

Affiliation:

Keywords: Catechol, Hydroquinone, Electrochemical synthesis, Thioimidazole, Cyclic voltammetry, Michael addition reaction.

Abstract: 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.

Cite this article as:

Nematollahi Davood, Davarani S.H. Saied, Mirahmadpour Pari and Varmaghani Fahimeh, Investigation of Electrochemically Induced Michael Addition Reactions of Ortho- and Para-banzoquinones with 2-Mercaptobenzimidazole: Application to Electrosynthesis, Letters in Organic Chemistry 2014; 11(6) . https://dx.doi.org/10.2174/1570178611666140207220757