Electrochemical oxidation of quercetin in the presence of benzenesulfinic acids

作者: D Nematollahi , M Malakzadeh

DOI: 10.1016/S0022-0728(03)00188-8

关键词: Inorganic chemistrySulfonylElectrochemistryCyclic voltammetryNuclear chemistryReaction mechanismChemistryMichael reactionAcetonitrileNucleophileCoulometry

摘要: Electrochemical oxidation of quercetin has been studied in the absence and presence benzenesulfinic acids as nucleophiles an acetonitrile+water mixture, using cyclic voltammetry controlled-potential coulometry. The results indicate that o-quinone derived from participates a Michael addition reaction with to form corresponding sulfonyl derivatives. electrochemical synthesis these derivatives successfully performed at carbon rod electrodes undivided cell good yield purity.

参考文章(18)
Wolf Bors, Christa Michel, Manfred Saran, Flavonoid antioxidants: rate constants for reactions with oxygen radicals. Methods in Enzymology. ,vol. 234, pp. 420- 429 ,(1994) , 10.1016/0076-6879(94)34112-5
A. Brun, R. Rosset, Étude electrochimique de l'oxydation de la dihydroxy-3,4 phénylalanine (Dopa) Journal of Electroanalytical Chemistry. ,vol. 49, pp. 287- 300 ,(1974) , 10.1016/S0022-0728(74)80236-6
Catherine Rice-Evans, Lester Packer, Flavonoids in health and disease Marcel Dekker. ,(2003) , 10.1201/9780367803681
L. Papouchado, G. Petrie, R.N. Adams, Anodic oxidation pathways of phenolic compounds Journal of Electroanalytical Chemistry. ,vol. 38, pp. 389- 395 ,(1972) , 10.1016/S0022-0728(72)80349-8
Michael D. Ryan, Alice Yueh, Wen‐Yu Chen, The Electrochemical Oxidation of Substituted Catechols Journal of The Electrochemical Society. ,vol. 127, pp. 1489- 1495 ,(1980) , 10.1149/1.2129936
Lucien. Papouchado, Glen. Petrie, J. H. Sharp, Ralph N. Adams, Anodic hydroxylation of aromatic compounds Journal of the American Chemical Society. ,vol. 90, pp. 5620- 5621 ,(1968) , 10.1021/JA01022A061
Howard P. Hendrickson, Arlen D. Kaufman, Craig E. Lunte, Electrochemistry of catechol-containing flavonoids Journal of Pharmaceutical and Biomedical Analysis. ,vol. 12, pp. 325- 334 ,(1994) , 10.1016/0731-7085(94)90007-8
Thomas E. Young, John R. Griswold, Matthew H. Hulbert, Melanin. I. Kinetics of the oxidative cyclization of dopa to dopachrome. Journal of Organic Chemistry. ,vol. 39, pp. 1980- 1982 ,(1974) , 10.1021/JO00927A057