Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) and N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide as Efficient Reagents to Direct Oxidative Conversion of Thiols and Disulfide to Sulfonyl Chlorides

Abstract

Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, IranReceived July 6, 2011, Accepted August 19, 2011Poly(N,N'-Dichloro-N-ethyl-benzene-1,3-disulfonamide) (PCBS) and N,N,N',N'-Tetrachlorobenzene-1,3-disulfonamide (TCBDA) were found to be a mild and efficient reagent for the direct oxidative conversion ofsulfur compounds to the corresponding arenesulfonyl chlorides in good to excellent yields through theoxidative chlorination. The overall process is simple, practical, and it provides convenient access to a varietyof aryl or heteroarylsulfonyl chlorides. The mild reaction conditions and the broad substrate scope render thismethod attractive, and complementary to existing syntheses of aryl or heteroarylsulfonyl chlorides. Key Words : Oxidative chlorination, Sulfonyl chloride, Thiol, Disulfide, N-Chloro sulfonamidesIntroductionAryl and heteroarylsulfonyl chlorides were an importantclass of compounds primarily used in the preparation ofsulfonamides. Sulfonamide motifs are prevalent in a varietyof biologically active compounds with a broad range ofbiological and pharmaceutical activities including inhibitionof carbonic anhydrase,