Anodic Cyclization-Rearrangement of Methoxybibenzyls to Dihydrophenanthrones

J R Falck, L. L. Miller, F. R. Stermitz

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29 Scopus citations

Abstract

Anodic oxidations were performed in acetonitrile at platinum using controlled potentials. 2-Methyl-3′,4,4′,5-tetramethoxybibenzyl was converted in 98 % yield to 9,10-dihydro-10a-methyl-2,6,7-trimethoxy-3(10aH)-phenanthrone. 2-Methyl-2′,4,5′,5-tetramethoxybibenzyl produced 9,10-dihydro-10a-methyl-2,5,8-trimethoxy-3(10aH)-phenanthrone in 88% yield. 9,10-Dihydro-10a-methyl-2-ethoxy-6,7-dimethoxy-3(10aH)-phenanthrone was correspondingly formed from 2-methyl-3′,4′, 5-trimethoxy-4-ethoxybibenzyl. 2-Methyl-4,5-dimethoxybibenzyl did not cyclize under these conditions. A mechanism rationalizing these products as well as cyclic voltammetric data is proposed.

Original languageEnglish (US)
Pages (from-to)2981-2986
Number of pages6
JournalJournal of the American Chemical Society
Volume96
Issue number9
DOIs
StatePublished - May 1 1974

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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