Dimethyldioxirane oxidation of (E,E)-cinnamylideneacetophenones

Albert Lévai, Artur M.S. Silva, José A.S. Cavaleiro, Amás Patonay, Vera L.M. Silva

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16 Citations (Scopus)

Abstract

The (E,E)-cinnamylideneacetophenones 1a-f were oxidised by isolated dimethyldioxirane (DMD, as acetone solution) at room temperature, giving diastereomeric mixtures of the α,β:γ,δ-diepoxides 3a-f when an excess of oxidant was used. α,β-Monoepoxides, found as minor components of the reaction, could be detected in only two cases (2c,d) when one equivalent of DMD was used. Dimethyldioxirane oxidation of (E,E)-2′-hydroxycinnamylideneacetophenones (4a-d) led to the formation of diastereomeric mixtures of the α,β:γ,δ-diepoxides 6a-d as well as to the γ,δ-monoepoxides 5a-d as minor products. The diepoxides 6a-d were transformed into the isolable coumaranone derivatives 7a-d during their chromatographic purification. All the compounds described have been fully characterised by NMR spectroscopy.

Original languageEnglish
Pages (from-to)3213-3219
Number of pages7
JournalEuropean Journal of Organic Chemistry
Issue number17
DOIs
Publication statusPublished - Sep 2001

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Keywords

  • Enones
  • Epoxidation
  • Ketones
  • NMR spectroscopy

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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