Chemistry of Organic Chloramines. Formation of Arenesulfonamides by Derivatization of Organic Chloramines with Sodium Arenesulfinates

Article abstract of DOI:10.1021/jo00338a005

Organic chloramines react rapidly with sodium benzenesulfinate or sodium toluenesulfinate to form arenesulfonamides.Derivatization was carried out by three different methods, one involving derivatization of pure chloramines and two involving derivatization of the chloramines generated in situ by reaction of the amine with sodium hypochlorite.Seventeen arenesulfonamides whose amine precursors included primary and secondary aliphatic amines, aromatic amines, and amino acids were synthesized in poor to excellent yields depending on the method used.Effects of structure,stability, and water solubility of the chloramine precursors are discussed.Benzenesulfonyl chloride can be isolated from the reaction of 10^-4 M N-chloropiperidine with sodium benzenesulfinate.Competing hydrolysis of the sulfonyl chloride accounts for low yields of sulfonamide for dilute solutions of chloramine.