Electrochemical oxidation of 2,3-dimethylhydroquinone in the presence of 1,3-dicarbonyl compounds

Autor: Davood Nematollahi, Nahid Mashkouri Najafi, Mojtaba Shamsipur, Somayyeh Ramyar, Saied Saeed Hosseiny Davarani, Leila Masoumi
Rok vydání: 2006
Předmět:
Zdroj: The Journal of organic chemistry. 71(5)
ISSN: 0022-3263
Popis: The electrooxidation of 2,3-dimethylhydroquinone (1) has been studied in the presence of 2-phenyl-1,3-indandione (3a), 3-hydroxy-1H-phenalen-1-one (3b), and 2-chloro-5,5-dimethyl-1,3-cyclohexanedione (3c) as CH acid nucleophiles in water/acetonitrile (85/15) solution, using cyclic voltammetry and controlled-potential coulometry. The results indicate that p-benzoquinone, generated by electrochemically driven oxidation of the 2,3-dimethylhydroquinone (1), is scavenged by 3a−c, to give related products (5a, 9b, 8c) via various electrochemical mechanisms. The electrochemical syntheses of 5a, 9b, and 8c have been successfully performed in one-pot in an undivided cell using an environmentally friendly method with high atomic economy.
Databáze: OpenAIRE