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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.…”

“…Search for new sulfenylating agents effective toward N-H or N-M compounds is important from both preparative and theoretical viewpoints. In the preceding communication [1] it was shown that previously unknown N-arylsulfenyl-N,N'-bis(phenylsulfonyl)sulfinimidamides are effective sulfenylating agents with respect to thiols and that these compounds can be used for the preparation of both symmetric and asymmetric disulfides. Proceeding with studies in this line, in the present work we examined reactions of N-arylsulfenyl-N,N'-bis(phenylsulfonyl)-sulfinimidamides Ia and Ib with compounds having N-H or N-M bonds.…”

Convenient and efficient synthesis of functionalized unsymmetrical Z-alkenyl disulfanes

“… 3 Although many different methods exist for the preparation of unsymmetrical disulfanes, the most common approach involves substitution of a sulfenyl derivative with a thiol or thiol derivative. To date, the most commonly utilized sulfenyl derivatives are sulfenyl chlorides, 4 S -alkyl thiosulfates and S -aryl thiosulfates (Bunte salts), 5 S -alkylsulfanylisothioureas, 6 benzothiazol-2-yl disulfanes, 7 benzotriazolyl sulfanes, 8 dithioperoxyesters, 9 (alkylsulfanyl)dialkylsulfonium salts, 10 2-pyridyl disulfanes and derivatives, 11 N -alkyltetrazolyl disulfanes, 12 sulfenamides, 13 sulfenyldimesylamines, 14 sulfenyl thiocyanates, 15 4-nitroarenesulfenanilides, 16 thiolsulfinates and thiosulfonates, 17 sulfanylsulfinamidines, 18 thionitrites, 19 sulfenyl thiocarbonates, 20 thioimides, 21 and thiophosphonium salts. 22 Other practical procedures involve the reaction of a thiol with a sulfinylbenzimidazole, 23 a rhodium-catalyzed disulfide exchange, 24 an electrochemical method, 25 the ring opening of an aziridine using tetrathiomolybdate in the presence of a symmetrical disulfane, 26 or the use of diethyl azodicarboxylate (DEAD) 27 or a solid support 28 in a sequential coupling of two different thiol groups.…”

DDQ-mediated synthesis of functionalized unsymmetrical disulfanes

“…and thiolsulfonates, [28][29][30][31] sulfanylsulnamidines, 32 thionitrites, 33 sulfenylthiocarbonates, 34 thioimides, [35][36][37] and thiophosphonium salts. 38 Other practical procedures involve the reaction of a thiol with a sulnylbenzimidazole, 39 the rhodium-catalyzed disulde exchange, 40,41 an electrochemical method, 42 ring opening of aziridines using tetrathiomolybdate in the presence of symmetrical disulfanes, 43,44 and the use of diethyl azodicarboxylate (DEAD) 45 or a solid support 46 in a sequential coupling of two different thiol groups.…”