Dimethyldioxirane Oxidation of Exocyclic (E,E)-Cinnamylideneketones

摘要: Exocyclic (E,E)-cinnamylideneketones were oxidized by an excess of isolated dimethyldioxirane (DMDO, in acetone solution) at room temperature, providing diastereomeric mixtures the α,β:γ,δ-diepoxides. In case derivatives bearing ortho-nitrocinnamylidene moiety, α,β-monoepoxides also as minor products. The structures all new compounds and stereochemistry monoepoxides diepoxide diastereomers established NMR studies.