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.
|Number of pages||7|
|Journal||European Journal of Organic Chemistry|
|Publication status||Published - Sep 2001|
- NMR spectroscopy
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry