Oxidation of phenols. Part 5. Oxidation of 2-allyl-4-t-butylphenol

Abstract

Oxidation of 2-allyl-4-t-butylphenol with manganese(III) acetylacetonate afforded the spiroacetal (4). There was no evidence for products arising from intramolecular attack of the phenoxyl radical centre on the double bond of the allyl group. The reaction of 2-allyl-4-t-butylphenol with vanadium oxide trichloride gave 2-allyl-4-chlorophenol and 2-allyl-4,6-dichlorophenol. The reactions of several other phenols with vanadium oxide trichloride in which chlorodealkylation is a common feature are also reported.