Electrochemical oxidation of 2,3-dimethylhydroquinone in the presence of 1,3-dicarbonyl compounds.
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.
Department of Chemistry, Shahid Beheshti University, Tehran, Iran.
Saied Saeed
SS
Hosseiny Davarani
Davood
D
Nematollahi
Mojtaba
M
Shamsipur
Nahid Mashkouri
NM
Najafi
Leila
L
Masoumi
Somayyeh
S
Ramyar
D001572:Benzofurans / Q000737:chemistry; D004563:Electrochemistry; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction
D001572:Benzofurans; D006873:Hydroquinones; C516077:2,3-dimethylhydroquinone