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

Authors :
Hosseiny Davarani SS
Nematollahi D
Shamsipur M
Najafi NM
Masoumi L
Ramyar S
Source :
The Journal of organic chemistry [J Org Chem] 2006 Mar 03; Vol. 71 (5), pp. 2139-42.
Publication Year :
2006

Abstract

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.

Details

Language :
English
ISSN :
0022-3263
Volume :
71
Issue :
5
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
16497004
Full Text :
https://doi.org/10.1021/jo0523767