Mechanistic study of electrochemical oxidation of 2,5-dihydroxybenzoic acid and 3,4-dihydroxybenzaldehyde in the presence of 3-hydroxy-1H-phenalene-1-one.
The mechanism of the electrochemical oxidation of 2,5-dihydroxybenzoic acid and 3,4-dihydroxybenzaldehyde in the presence of 3-hydroxy-1H-phenalene-1-one as a nucleophile has been studied in water/acetonitrile (80/20 v/v) solution using cyclic voltammetry and controlled-potential coulometry methods. The results indicate that the quinones derived from oxidation of 2,5-dihydroxybenzoic acid and 3,4-dihydroxybenzaldehyde participate in Michael addition reactions with 3-hydroxy-1H-phenalene-1-one and via ECE and ECEC mechanisms convert to the different products, with good yield under controlled potential conditions, at carbon electrode.
Nematollahi
Davood
D
Faculty of Chemistry, Bu-Ali-Sina University, Hamadan, Iran. nemat@basu.ac.ir
Amani
Amaneh
A
D001547:Benzaldehydes / Q000737:chemistry*; D002396:Catechols / Q000737:chemistry*; D004563:Electrochemistry; D005841:Gentisates / Q000737:chemistry*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D043803:Phenalenes / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D013055:Spectrophotometry, Infrared
D001547:Benzaldehydes; D002396:Catechols; D005841:Gentisates; D007202:Indicators and Reagents; D043803:Phenalenes; C005581:protocatechualdehyde; C010925:2,5-dihydroxybenzoic acid