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

ISSN: 1875-6255 (Online)
ISSN: 1570-1786 (Print)


Volume 11, 10 Issues, 2014


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Letters in Organic Chemistry

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Editor-in-Chief:
Miguel Yus
Universidad de Alicante Apdo
Alicante
Spain


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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 and Fahimeh Varmaghani

Affiliation: Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran, 65178-38683.

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

Volume: 11
Issue Number: 6
First Page: 398
Last Page: 402
Page Count: 5
DOI: 10.2174/1570178611666140207220757
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