Oxidation of o-methoxyphenols with a hypervalent iodine reagent: Improved synthesis of asatone and demethoxyasatone

László Kürti, László Szilágyi, Sándor Antus, Mihály Nógrádi

Research output: Contribution to journalArticle

19 Scopus citations

Abstract

Oxidation of the 2-methoxyphenols 1c-f with phenyliodonium(III) diacetate (PIDA) in methanol resulted in the formation of the cyclohexa-2,4- dienones 4c-f, which dimerized spontaneously to a single product (5c-f) in each case. Using this method the synthesis of asatone (5a) and its demethoxy analogue (5b) was also accomplished starting from the readily available phenol derivatives 1a and 1b, respectively.

Original languageEnglish (US)
Pages (from-to)2579-2581
Number of pages3
JournalEuropean Journal of Organic Chemistry
Issue number10
StatePublished - Oct 1 1999

Keywords

  • Asatone
  • Cyclohexa-2,4- dienones
  • Dimerization
  • Hypervalent iodine
  • Oxidation
  • Phenols

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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