FRAGMENTATION REACTION OF YLIDE .7. REACTION OF OXAZIRIDINES WITH NUCLEOPHILIC-REAGENTS

The reaction of oxaziridines with nucleophilic reagents was studied to obtain clues toward understanding their biological properties. 2-Methyl-3-phenyloxaziridine and triethylamine gave hexamethylenetetramine as the main product, Oxaziridine also gave trimethylhydrazine or azomethane in good yield on reaction with dimethylamine or methylamine, respectively. In the reaction with l-methyl-2-p)-chlorophenylaziridine, the oxaziridine showed a double fragmentation reaction forming azomethane, p-chlorostyrene, and benzaldehyde. 2-Methyl-3-phenyloxaziridine also reacted with triphenylphosphine to give triphenylphosphinemethylimine and with thiophenol to give 7V-methylbenzenesulfenamide in a vigorous reaction even at -20 °C. The reactions were discussed as SN2 fragmentation reactions of the three-membered ring of oxaziridines. © 1979, American Chemical Society. All rights reserved.