Alkylation of salts of N-nitroarenesulfonamides by alkyl halides

Abstract

1. Primary and secondary alkyl bromides and iodides react with the silver salts of N-nitroarenesulfonamides to form usually a mixture of N-and O-alkylation products. Tertiary alkyl iodides, according to the structure of the alkyl group, afford either the nitroamides or O-alkylation products. 2. The contribution of O-alkylation increases on passing from primary to secondary alkyl halides and from iodides to bromides, and decreases when electron-acceptor groups are introduced into the aromatic ring of the N-nitroarenesulfonamide. 3. The contribution of O-alkylation increases on passing from protic polar or aprotic dipolar to nonpolar solvents.