ChemInform Abstract: IMINATION OF SULFUR‐CONTAINING COMPOUNDS. XIV. ARENESULFONYLIMINATION OF N‐ARENESULFONYL‐2,4‐DINITROBENZENE‐ AND ‐2,4,6‐TRINITROBENZENESULFENAMIDES

Imination of Sulfur-Containing Compounds: XXXVI. A New Method of Synthesis and Oxidative Arylsulfonylimination of Sulfenamides

“…Arenesulfinimidamides VIa-VId were reported previously [1,13,15,26]; they were identified by the melting points (by mixing with authentic samples) and IR and mass spectra. The IR spectrum of VIa contains two strong absorption bands in the region 3250-3350 cm -1 , which belong to stretching vibrations of the free NH 2 group.…”

“…N-Chlorobenzenesulfonamide sodium salt, 0.001 mol, was added to a solution of 0.001 mol of sulfenamide IIa in 10 ml of acetone, and the mixture was stirred until complete disappearance of active chlorine. The mixture was filtered, the filtrate was evaporated in air, and the residue was recrystallized from benzene to obtain 0.26 g (92%) of N-phenylsulfonylbenzenesulfinimidamide (VIa) which was identified by comparing with an authentic sample [13] and by IR spectroscopy. The reaction with sulfenamide IIb was performed in a similar way to isolate 0.22 g (62%) of N-p-tolylsulfonyl-N,N'-diethylbenzenesulfinimidamide (VIb) which was identified by the melting point [26].…”

“…Another equally important reaction leading to sulfinimidamides is oxidative imination of sulfenamides with N-halo derivatives [4,5]. Here, the ability of sulfenamides to undergo imination with N-halo compounds is determined by the structure of the initial sulfenamide [19], nucleophilicity of the sulfur atom therein [20,21], acidity of the substrate [22], strength of the C-S bond [23], solvent nature [13,24], and other factors which should be taken into account in each particular case. Therefore, it was interesting to study oxidative imination of sulfenamides IIa and IIb with N-chloro-arenesulfonamide sodium salts.…”

“…By reaction of compounds Ia and Ib with arenesulfonamide sodium salts in anhydrous acetone we obtained N-(arylsulfonyl)arenesulfenamides IVa and IVb and N,N'-bis(arylsulfonyl)arenesulfinimidamide sodium salts Va and Vb (Scheme 2). Sulfenamides IIa-IIc, IVa, and IVb were reported previously [13][14][15]; they were identified by the melting points (by mixing with authentic samples) or refractive indices (for liquid substances). N-(Arylsulfenyl)-N,N'-bis(phenylsulfonyl)sulfinimidamides Ia and Ib were prepared by the procedure developed by us previously [16,17], namely by oxidative imination of sodium benzenethiolates with N,N-dichlorobenzenesulfonamide in carbon tetrachloride (Scheme 3).…”