Electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives

• Published in: Journal of electroanalytical chemistry (Lausanne, Switzerland) Vol. 577; no. 2; pp. 197 - 203
• Main Authors: Nematollahi, D., Hesari, M.
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 01.04.2005; Elsevier Science
• Subjects: Amino-substituted 1,2-benzoquinone; Catechol; Chemistry; Cyclic voltammetry; Dibenzylamine; Electrochemical synthesis; Electrochemistry; Exact sciences and technology; General and physical chemistry; Kinetics and mechanism of reactions; Cyclic voltammetry; Dibenzylamine; Catechol; Amino-substituted 1,2-benzoquinone; Electrochemical synthesis; Pyrocatechol derivatives; Quinone; Benzoquinone derivatives; Carbon; Diphenols; Electrodes; Mixed solvent; Medium effect; Acetonitrile; Reaction mechanism; Benzenic compound; Oxidation; Kinetics; Hydroorganic solvent; Electrochemical reaction; Chemical synthesis; Organic compounds; Glassy state
• ISSN: 1572-6657; 1873-2569
• DOI: 10.1016/j.jelechem.2004.11.031

The electrooxidation of 3-substituted catechols ( 1) has been studied in the presence of dibenzylamine ( 3) in water + acetonitrile (90/10) solution, using electrochemical and spectroelectrochemical methods. The o-benzoquinones ( 2) derived from catechols ( 1) participate in Michael addition reactions with dibenzylamine ( 3) to form the corresponding monoamino-substituted o-benzoquinones ( 5). We propose a mechanism for the electrode process. An efficient electrochemical synthesis of amino-substituted 1,2-benzoquinone derivatives ( 5) has been performed at a carbon rod electrode in a two-compartment cell.