Chemical & Pharmaceutical Bulletin 2010-01-01

Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid. Synthesis and kinetic evaluation.

Davood Nematollahi, Maryam Bamzadeh, Hasan Shayani-Jam

Index: Chem. Pharm. Bull. 58(1) , 23-6, (2010)

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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 (k(obs)) 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.