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Synthesis 1992; 1992(1/2): 49-51
DOI: 10.1055/s-1992-34184
short paper
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Direct Epoxidation of (E)-2′-Hydroxychalcones by Dimethyldioxirane

Waldemar Adam* , Joachim Bialas, Lazaros Hadjiarapoglou, Támas Patonay
  • *Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-8700 Würzburg, Germany
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Publication Date:
18 September 2002 (online)

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The synthesis of α,β-epoxy-2′-hydroxychalcones (3-aryl-2,3-epoxy-1-(2-hydroxyaryl)propanones) 2 by direct epoxidation of (E)-2′-hydroxychalcones [(E)-3-aryl-1-(2-hydroxyaryl)propenone] 1 with dimethyldioxirane at subambient temperatures is reported. These acid- and base-sensitive epoxides, which have been hitherto difficult to prepare, were isolated in excellent yields and were completely characterized by spectral and microanalytical data. The now readily available 2′-hydroxy substituted chalcone oxides may serve as convenient precursors to flavonoid-type natural products.