Aspects of aromatic amine and phenol oxidation: I. The mechanism of alkoxy elimination concurrent with electrooxidation of methoxy-substituted aromatic compounds
✍ Scribed by Donald W. Leedy
- Publisher
- Elsevier Science
- Year
- 1973
- Weight
- 160 KB
- Volume
- 45
- Category
- Article
- ISSN
- 0022-0728
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✦ Synopsis
We have proposed previously an overall mechanism of methoxy elimination which occurs concurrent with electrooxidation of N-phenyl-p-anisidine 1. A similar mechanism was proposed in an earlier communication for the oxidation ofp-methoxyphenol to quinone 2. However, little has been said concerning the details of hydrolysis of the alkoxy carbonium ion intermediate common to these reactions. Similar mechanistic studies have been undertaken in the recent literature of the oxidation processes of ester and ether derivatives of 1,4-hydroquinone systems 3'4. Such interest stems from the possible roles these systems play in electron transport, energy conservation, and oxidative phosphorylation reactions 5. Important results in this area have resulted from the studies of Dtirckheimer and Cohen 6 and, more recently, by the work of Marcus and Hawley 7.
The results of these studies make it possible to propose a mechanism involving the alkoxy carbonium ion for the oxidation of p-methoxyphenol to quinone: