Anodic cyclization-rearrangement of methoxybibenzyls to dihydrophenanthrones

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

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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
StatePublished - 1974

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Cyclization
Anodic oxidation
Platinum
Acetonitrile
acetonitrile

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Anodic cyclization-rearrangement of methoxybibenzyls to dihydrophenanthrones. / Falck, J R; Miller, L. L.; Stermitz, F. R.

In: Journal of the American Chemical Society, Vol. 96, No. 9, 1974, p. 2981-2986.

Research output: Contribution to journalArticle

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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.",
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N2 - 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.

AB - 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.

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