Epoxidation of Vinylamides by Dimethyldioxirane: First Spectral Evidence for Enamide Oxides

Article abstract of DOI:10.1016/0040-4020(95)00792-7

The oxidation of the (E)- and (Z)-N-propenylbenzamides (1) by dimethyldioxirane (DMD) in acetone solution leads to the α-amido epoxides 2, which were detected by low-temperature NMR spectroscopy; above -50 deg C they dimerize to the diastereomeric dioxane