BASE CATALYZED OXYGENATION OF HINDERED PHENOLS. SYNTHESIS OF 4-HYDROXY-5,6-EPOXY-2-CYCLOHEXENONES (EPOXY-p-QUINOLS)
- 5 July 1974
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 3 (7) , 667-670
- https://doi.org/10.1246/cl.1974.667
Abstract
Oxygenation of 2,6-di-t-butyl-4-alkylphenols catalyzed by Bu tOK in aprotic solvents has been found newly to form 4-hydroxy-5,6-epoxy-2-cyclohexenones (2) in excellent yield. A mechanism by which 2 is formed envisaging intramolecular participation of the π-system in the degradation of 4-oxo-2,5-cyclohexadienyl peroxide ion (11) primarily formed as transient intermediate is discussed. 2,4-Di-t-butylphenols also gave epoxy-p-quinols in the same system.Keywords
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