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Letters in Organic Chemistry
ISSN (Print): 1570-1786
ISSN (Online): 1875-6255
VOLUME: 11
ISSUE: 6
DOI: 10.2174/1570178611666140207220757      Price:  $58









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

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Author(s): Davood Nematollahi, Saied S.H. Davarani, Pari Mirahmadpour and Fahimeh Varmaghani
Pages 398-402 (5)
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.
Graphical Abstract:
Keywords:
Catechol, Hydroquinone, Electrochemical synthesis, Thioimidazole, Cyclic voltammetry, Michael addition reaction.
Affiliation:
Faculty of Chemistry, Bu-Ali Sina University, Hamedan, Iran, 65178-38683.