Oxidation of alkoxyphenols. XXIX. Phototautomerism and dinierization of 4,6-Di-t-butyl-4a-hydroxy-8-methoxydibenzofuran-2(4aH)-one

Abstract

In solution in non-polar solvents the title compound undergoes photochemical ring opening to its hydroxyphenylquinone tautomer. Oxidation of 3,3'-di-t-butyl-5,5'-dimethoxybiphenyl-2,2'-diol withvanadium oxytrifluoride in the presence of trifluoroacetic acid yields bisdibenzofurans. The crystal structures of 4,4',6,6'-tetra-t-butyl-2',8-dimethoxy-1,1'-bisdibenzofuran-2,8'-diol and of 4,6-di-t-butyl-4a-hydroxy-8-methoxydibenzofuran-2(4aH)-one have been determined.