Acyl nitroxides. Part I. Synthesis and isolation

Abstract

Acylation of N-t-butylhydroxylamine occurs predominantly on oxygen. With acetic anhydride, essentially pure O-acetyl-N-t-butylhydroxylamine is formed. This can be acylated on nitrogen, and the O-acetyl-group removed to give a variety of hydroxamic acids RCON(Bu^t)OH which can be oxidised to isolable acyl nitroxides RCON(Bu^t)O·(R = alkyl, aryl, alkoxy, or dialkylamino). Other oxygen-protecting groups for N-t-butylhydroxyl-amine are discussed. The reactions have been extended to include syntheses of a number of acyl nitroxide bi-radicals.