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Mechanism of action of base-catalyzed oxygenation of phenol derivatives
- Issue Date
- Nov-2005
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- autooxidation; phenolate; mechanism; radical
- Citation
- TETRAHEDRON LETTERS, v.46, no.45, pp 7721 - 7723
- Pages
- 3
- Journal Title
- TETRAHEDRON LETTERS
- Volume
- 46
- Number
- 45
- Start Page
- 7721
- End Page
- 7723
- ISSN
- 0040-4039
- Abstract
- Cyclopropyl derivative of 2,6-di-tert-butylphenol is synthesized as a probe to investigate the mechanism of base-catalyzed autooxidation of phenol derivatives. Our study indicates that one electron reduction of molecular oxygen from phenolate gives phenoxyl radical 3, a key intermediate of autooxidation. The coupling of phenoxyl radical and superoxide radical gives peroxylate anion 4 and produces the final epoxy alcohol adduct 6. (c) 2005 Published by Elsevier Ltd.
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Collections - College of Natural Sciences > Department of Chemistry > 1. Journal Articles
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