Electrochemical behavior of catechol in the presence of 2-methyl-1,3-cyclopentanedione: application to electrosynthesis

Abstract  Electro-oxidation of catechol in the presence of 2-methyl-1,3-cyclopentanedione as a nucleophile was investigated in water–acetonitrile (90:10 v/v) solution. The results indicate that the o-benzoquinone electrogenerated participates in a Michael addition reaction with this nucleophile. The electrosynthesis of 2-(3,4-dihydroxyphenyl)-2-methylcyclopentane-1,3-dione was carried out. The product was characterized by NMR, MS, FT-IR, and elemental analysis. An EC mechanism was deduced from voltammetric and spectroscopic data. Also, the Michael addition reaction rate constant (k _m) was estimated using digital simulation of voltammograms. Graphical abstract   Electronic supplementary material  The online version of this article (doi:) contains supplementary material, which is available to authorized users.