Mechanism of action of base-catalyzed oxygenation of phenol derivatives |
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Authors: | Duck-Hyung Lee Seokwon Jung Seung Wook Ham |
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Institution: | a Chemistry Department, Sogang University, Seoul 121-742, Republic of Korea b Department of Chemistry, Chung-Ang University, Seoul 156-756, Republic of Korea |
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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. |
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Keywords: | Autooxidation Phenolate Mechanism Radical |
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