Selective formation of aminoxyls or oxaziridines by oxidation of 2,2,4,4-tetrasubstituted oxazolidines

Article abstract of DOI:10.1016/0040-4020(95)00899-3

The reactivity of 2,2,4,4-tetrasubstituted-1,3-oxazolidines 1 with m-chloroperbenzoic acid was reinvestigated. Aminoxyls 5 are isolated in good yields in ether at -15°C, or in anhydrous dichloromethane at 0°C. Oxaziridines 4 are promoted at room temperature, or in the presence of an acid. In any case, short reaction times prevented the degradation of aminoxyls and oxaziridines. The competition between oxaziridines 4 and aminoxyls 5 is ruled by the oxazolidine imine equilibrium.