N ‐Aryl‐ O ‐acylhydroxylamines: Preparation by O ‐Acylation or N → O Transacylation and Reaction with Amines; Model Reactions for Key Steps Connected with the Carcinogenicity of Aromatic Amines

That aromatic amines Aryl‐NH 2 are carcinogenic is (more or less) common knowledge nowadays. N ‐Aryl‐ O ‐acetylhydroxylamines 2 , which are active metabolites thereby, and other O ‐acylhydroxylamines of this type have now been prepared by O ‐acylation of arylhydroxylamines or by transacylation from the hydroxamine acids 1. The compounds 2 react in vitro as electrophilic aminating reagents with amines as nucleophiles to give hydrazines 3. 2 could react analogously in vivo with binucleophiles like DNA.