Novel, base-promoted reaction of N-alkoxycarbonyl-O-(halosubstituted 4-nitrophenyl)hydroxylamines

This paper describes base-promoted reactions of N-alkoxycarbonyl-O-(nitrophenyl)hydroxylamines which contain a halogen attached to the aromatic ring. The reaction is promoted under mild conditions (NaHCO3 or K2CO3) and provides the N-alkoxycarbonyl-N-hydroxyaniline. In a crossover experiment, some scrambling was observed which suggests that the reaction is inter- and intramolecular in nature. N-Boc-(2,6-di-Cl-4-NO2-phenyl)hydroxylamine was also found to N-Boc aminate Bn2NH to form the protected hydrazine in modest yield.