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

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

Journal Name: Letters in Organic Chemistry

Volume 11 , Issue 6 , 2014

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Graphical 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.

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

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Article Details

Year: 2014
Page: [398 - 402]
Pages: 5
DOI: 10.2174/1570178611666140207220757
Price: $65

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