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.
Letters in Organic Chemistry
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.
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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
DOI https://dx.doi.org/10.2174/1570178611666140207220757 |
Print ISSN 1570-1786 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6255 |
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