CONVENIENT HALODEAMINATION AND HYDRODEAMINATION OF PRIMARY AMINES

Treatment of p-toluenesulfonamides of primary amines with 2 equiv of chloroamine at room temperature in the presence of base leads to reductive deamination. If excess chloroamine is present, the corresponding alkyl or aryl halides are obtained instead in good yields. Both reactions presumably proceed via tosylhydrazine and diazene intermediates; the course of the reaction is often governed by steric hindrance. Treatment of the isolated tosylhydrazine intermediate with base and chloroamine, bromine, or iodine also leads to the corresponding halides in very good yields.