Electrooxidation of 4-methylcatechol in the presence of barbituric acid derivatives

• Published in: Electrochimica acta Vol. 50; no. 18; pp. 3648 - 3654
• Main Authors: Nematollahi, Davood, Tammari, Esmail
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 10-06-2005; Elsevier
• Subjects: 4-Methylcatechol; Barbituric acid; Chemistry; Cyclic voltammetry; Electrochemical synthesis; Electrochemistry; Exact sciences and technology; General and physical chemistry; Kinetics and mechanism of reactions; Quinone methide; Cyclic voltammetry; Barbituric acid; Quinone methide; 4-Methylcatechol; Electrochemical synthesis; Reaction intermediate; Nucleophilic reaction; Nitrogen heterocycle; Experimental study; ECEC mechanism; Six membered ring; Oxidative degradation; Phenols; Quinonemethide; Aqueous solution; Electrochemical reaction
• ISSN: 0013-4686; 1873-3859
• DOI: 10.1016/j.electacta.2005.01.007

Electrooxidation of 4-methylcatechol (
1) in the presence of 1,3-dimethylbarbituric acid (
2a) and 1,3-diethylthiobarbituric acid (
2b) as nucleophiles has been studied in detail by cyclic voltammetry and controlled-potential coulometry. The results indicate that
1 can be oxidized to its related
o-benzoquinone (
1a) and without conversion to its quinone methide tautomeric form, via an ECEC mechanism pathway, is converted to barbiturate derivatives (
5a–
b). The electrochemical synthesis of
5a–
b have been successfully performed in one-pot in an undivided cell.