Thallium in Organic Synthesis. XLII. Direct Oxidation of 4-Substituted Phenols to 4,4-Disubstituted Cyclohexa-2,5-Dienones Using Thallium(III) Nitrate

Alexander McKillop, David H. Perry, Mark Edwards, Sándor Antus, Loránd Farkas, Mihály Nógrádi, Edward C. Taylor

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162 Citations (Scopus)

Abstract

Oxidation of hydroquinones with 1 equiv, and 2,6-disubstituted phenols with 2 equiv, of thallium(III) nitrate (TTN) in methanol gives the corresponding p-benzoquinones in high yield. Oxidation of a variety of 4-alkyl- and 4-alkoxyphenols with 1 equiv of TTN in either methanol or trimethyl orthoformate (TMOF), on the other hand, gives 4-alkyl-4-methoxy- and 4,4-dimethoxycyclohexa-2,5-dienones in moderate to excellent yield. Formation of cyclohexadienones under these conditions is postulated to proceed via ipso thallation.

Original languageEnglish
Pages (from-to)282-287
Number of pages6
JournalJournal of Organic Chemistry
Volume41
Issue number2
DOIs
Publication statusPublished - Jan 1 1976

ASJC Scopus subject areas

  • Organic Chemistry

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