Oxidation of alkoxyphenols. Part XIV. Thermal rearrangements of some aryloxycyclohexadienones
Abstract
When gently heated, the p-aryloxycyclohexadienone obtained by oxidation of 5-methoxy-2,4-di-t-butylphenol, rearranges to 2,2′-dihydroxy-6,6′-dimethoxy-3,3′,5,5′-tetra-t-butylbiphenyl. Under similar conditions the analogous dienone derived from 4-methoxy-2,5-di-t-butylphenol gives the trimeric 2,4-diaryloxydienone, the dimeric o-aryloxyphenol, and the parent phenol. Evidence is presented in support of a suggested mechanism for this reaction. Electron spin resonance spectra obtained from these and related aryloxydienones are described.