EPOXIDATION OF VINYLAMIDES BY DIMETHYLDIOXIRANE - FIRST SPECTRAL EVIDENCE FOR ENAMIDE OXIDES

Authors
ADAM W REINHARDT D REISSIG HU PAULINI K
Citation
W. Adam et al., EPOXIDATION OF VINYLAMIDES BY DIMETHYLDIOXIRANE - FIRST SPECTRAL EVIDENCE FOR ENAMIDE OXIDES, Tetrahedron, 51(45), 1995, pp. 12257-12262
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
45
Year of publication
1995
Pages
12257 - 12262
Database
ISI
SICI code
0040-4020(1995)51:45<12257:EOVBD->2.0.ZU;2-9
Abstract
The oxidation of the (E)- and (Z)-N-propenylbenzamides (1) by dimethyl dioxirane (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 prese nce of methanol they are trapped to form the hemiaminal 4, while mCPBA cleaves them to N-formylbenzamide and acetaldehyde.