Oxidation of alkoxyphenols. XXIX phototautomerism and dimerization of 4,6-Di-t-butyl-4a-hydroxy-8-methoxy-dibenzofuran-2(4aH)-one

Frank R. Hewgill, Colin L. Raston, Brian W. Skelton, Rauleigh J. Webb, Allan H. White

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)

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 with vanadium 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.

Original languageEnglish
Pages (from-to)1603-1614
Number of pages12
JournalAustralian Journal of Chemistry
Volume36
Issue number8
DOIs
Publication statusPublished - 1983
Externally publishedYes

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