Journal of Electroanalytical Chemistry, Vol.548, 41-47, 2003
Electrosynthesis of organic compounds. Part II: Electrooxidative amination of 1,4-dihydroxybenzene using some aliphatic amines
The electrooxidative amination of 1,4-dihydroxybenzene (1) to give 2,5-disubstituted benzoquinones, using dimethylamine, piperidine and morpholine, as nucleophiles has been studied using cyclic voltammetry and controlled potential coulometry. The results indicate that the above-mentioned amines react with electrochemically generated p-benzoquinone via a Michael-addition reaction leading to 2,5-diamino-substituted benzoquinones. Products were obtained in good yield and purity, and were characterized by spectroscopic methods and elemental analysis. (C) 2003 Elsevier Science B.V. All rights reserved.
Keywords:electrooxidative amination;cyclic voltammetry;Michael addition;p-benzoquinone;dimethylamine;piperidine;morpholine