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