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1193674 
Journal Article 
EPOXIDATION OF VINYLAMIDES BY DIMETHYLDIOXIRANE - FIRST SPECTRAL EVIDENCE FOR ENAMIDE OXIDES 
Adam, W; Reinhardt, D; Reissig, HU; Paulini, K 
1995 
1 
Tetrahedron
ISSN: 0040-4020 
51 
45 
12257-12262 
WOS:A1995TD21800008 
The oxidation of the (E)- and (Z)-N-propenylbenzamides (1) by dimethyldioxirane (DMD) in acetone solution leads to the alpha-amido epoxides 2, which were detected by low-temperature NMR spectroscopy, above -50 degrees C they dimerize to the diastereomeric dioxanes 3, in the presence of methanol they are trapped to form the hemiaminal 4, while mCPBA cleaves them to N-formylbenzamide and acetaldehyde. 
• Methanol (Non-Cancer)
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