Medium effects in unsymmetrical disulfides compounds synthesis from bunte salts

A novel reduction of sodium alkyl thiosulfates with InCl3(cat.)/Sm(0) system in aqueous media: Facile synthesis of disulfides

“…The results indicated that the reaction is relatively insensitive to the electronic nature of substituents on the aromatic rings. As starting material, the sodium alkyl thiosulfates are readily prepared from the reaction of sodium thiosulfate with suitable alkyl bromide under mild phase transfer catalysis conditions [13].…”

A Novel Method for the Direct Synthesis of Symmetrical and Unsymmetrical Sulfides and Disulfides from Aryl Halides and Ethyl Potassium Xanthogenate

“…S-alkyl sulfurothioates and S-aryl sulfurothioates was prepared according to the literature methods. 1,2 All reagents and solvents used in this work were obtained from Merck and were used without further purification. TLC analyses were conducted on Merck silica gel GF254 plates.…”

Convenient Synthesis of Functionalized Unsymmetrical Vinyl Disulfides and Their Inverse Electron-Demand Hetero-Diels-Alder Reaction

“…The most common synthesis of disulfide functionality is based on the nucleophilic substitution reaction of a sulfenyl derivative with a thiol or thiol derivative. The most frequently utilized electrophilic sulfenyl derivatives are: sulfenyl chlorides [ 23 , 24 ], S -alkylsulfanylisothioureas [ 25 , 26 ], S -alkyl thiosulfates and S -aryl thiosulfates (Bunte salts) [ 27 ], benzotriazolyl sulfanes [ 28 , 29 ], benzothiazol-2-yl disulfides [ 30 ], (alkylsulfanyl)dialkylsulfonium salts [ 31 , 32 ], dithioperoxyesters [ 33 ], 2-pyridyl disulfides and derivatives [ 34 , 35 ], sulfonamides [ 36 ], N -alkyltetrazolyl disulfides [ 37 ], sulfenyl thiocyanates [ 38 ], sulfenyldimesylamines [ 39 ], thiolsulfinates [ 40 ] and thiosulfonates [ 41 , 42 , 43 ], 4-nitroarenesulfenanilides [ 44 ], thionitrites [ 45 ], thioimides [ 46 ], sulfenyl sulfanylsulfinamidines [ 47 , 48 , 49 ], and thiophosphonium salts [ 50 ]. The disulfides can also be efficiently obtained by the reaction of a thiol with a sulfinylbenzimidazole [ 51 ], a disulfide exchange reaction promoted by rhodium catalyst [ 52 , 53 ], an electrochemical method [ 54 ], using tetrathiomolybdate in the presence of a symmetrical disulfide to promote a ring opening of an aziridine [ 55 , 56 ], or the application of diethyl azodicarboxylate (DEAD) [ 57 ] or a solid support [ 58 ] to promote a sequential coupling of two different thiols.…”