OXIDATION OF N-ALKYL-N'-TOSYLHYDRAZINES WITH BROMINE

Article abstract of DOI:10.1016/S0040-4020(01)88628-2

Oxidation of N-alkyl-N'-tosylhydrazines with bromine yield alkyl bromides, vicinal alkyl dibromides and traces of alcohols.The main products of primary hydrazines are monobromides whereas secondary hydrazines preferably produce dibromides.The reaction proceeds with evolution of nitrogen and hydrobromic acid and by the formation of intermediate sulfinic ester wich may be isolated.Various substrates were examined under different conditions to confirm the validity of the reaction mechanism hypothesized.