Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Electrochemical Oxidation of Catechols in the Presence of Phenyl-Meldrum's Acid. Synthesis and Kinetic Evaluation
Davood NematollahiMaryam BamzadehHasan Shayani-Jam
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JOURNAL FREE ACCESS

2010 Volume 58 Issue 1 Pages 23-26

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Abstract

Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile in aqueous solution has been studied in detail by means of cyclic voltammetry and controlled potential coulometry. The results indicate that the o-benzoquinone derived from catechols participates in Michael addition reaction with phenyl-Meldrum's acid to form corresponding products. We derived some new “highly oxygenated compounds with catechol ring” with good yields based on electrochemical oxidation in the controlled potential condition in aqueous solutions, without toxic reagents and solvents at carbon electrode in an undivided cell, using an environmentally friendly method. Furthermore, the observed homogeneous rate constants (kobs) of the chemical reaction between o-benzoquinone and phenyl-Meldrum's acid were estimated by comparing the experimental cyclic voltammetric curves with the digitally simulated ones.

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© 2010 The Pharmaceutical Society of Japan
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