23705-41-1Relevant articles and documents
Mild and general method for the synthesis of sulfonamides
Garcia Ruano, Jose Luis,Parra, Alejandro,Yuste, Francisco,Mastranzo, Virginia M.
, p. 311 - 319 (2008/12/22)
Reaction of methyl sulfinates with lithium amides followed by 3-chloroperoxybenzoic acid oxidation of the resulting sulfinamides provides primary, secondary, and tertiary alkane-, arene-and heteroarenesulfonamides in high yields. This constitutes a mild and facile experimental protocol that avoids the use of hazardous, unstable, or volatile reagents and does not affect the configurational stability of the amines. Georg Thieme Verlag Stuttgart.
Chemistry of Organic Chloramines. Formation of Arenesulfonamides by Derivatization of Organic Chloramines with Sodium Arenesulfinates
Scully, Frank E.,Bowdring, Katherine
, p. 5077 - 5081 (2007/10/02)
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.
