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Relevant academic research and scientific papers

Unsymmetrical disulfide and sulfenamide synthesis via reactions of thiosulfonates with thiols or amines

The reactivity of thiosulfonates with nucleophilic reagents was investigated. When reactions of thiosulfonates with thiols were performed, unsymmetrical disulfides were obtained in excellent yields. This procedure could employ numerous aryl or alkyl thiols. On the other hand, reactions of thiosulfonates with amines proceeded in the presence of a copper catalyst. The procedure was performed efficiently in air, and afforded the corresponding sulfenamides.

Cleavage of S-S bond by nitric oxide (NO) in the presence of oxygen: A disproportionation reaction of two disulfides

Disulfide bond was cleaved by a catalytic amount of nitric oxide in the presence of oxygen, which was confirmed by experiments employing two symmetrical disulfides. The reaction resulted in the formation of unsymmetrical disulfides in nearly 50% yields. The steric hindrance of alkyl disulfide slowed the reaction rate, and an electron-donating group on the aryl disulfide promoted the reaction. The substituent and S-nitrosothiol effects suggested that the reaction was initialized with an oxidative process by NO+.

Disproportionation reaction of disulfides promoted by nitric oxide (NO) in the presence of oxygen

Two disulfides brought about disproportionation reaction to afford an unsymmetrical disulfide in 50% yield with a catalytic amount of nitric oxide in the presence of oxygen. The reaction proceeded faster when alkyl disulfides were employed for the reaction, and the substituent effects suggested that the reaction commenced with an oxidative process.

Some Unusual Properties of Tris(2,6-dimethoxyphenyl)phosphine Sulfide and the Related Compounds

The title sulfide 3P=S reacted with acids to form a novel mercaptophosphonium salt X, solution thermolysis of which in the absence or presence of triphenylphosphine resulted in the unusual desulfurization to give the tertiary phosphonium salts X. (2,6)3P=S also reacted with alkyl iodides or bromides under mild conditions to give stable (alkylthio)phosphonium salts X (R=Me, Et, n-Bu), which reacted with thiols at room temperature in the presence of a catalytic amount of the tertiary phosphine (2,6)3P to give X and unsymmetrical disulfides.

Facile Synthesis of Alkylthiophosphonium Salts of Tris(2,6-dimethoxyphenyl)phosphine and Their Reactions with Thiols

Tris(2,6-dimethoxyphenyl)phosphine sulfide reacted with alkyl iodides or bromides under mild conditions to give stable alkylthiophosphonium salts, which reacted with thiols at room temperature in the presence of a catalytic amount of tris(2,6-dimethoxyphenyl)phosphine to give the tertiary phosphonium salt and unsymmetrical disulfides.

SYNTHESIS OF DISULPHIDES AND TRISULPHIDES via ORGANOSILICON COMPOUNDS

Silyl sulphides 2a-b smoothly react with thiolsulphinates 1a-c and thiolsulphonates 6a-c to give unsymmetrical disulphides under mild conditions and in very good yields.The "neutral" conditions used allow one to avoid any side reactions and subsequent randomization of the products.When bis(trimethylsilyl)sulphide, 8, is used, symmetrical trisulphides may be obtained under the same experimental conditions.

SILICON IN ORGANOSULPHUR CHEMISTRY. Part 2. SYNTHESIS OF UNSYMMETRICAL DISULPHIDES

Unsymmetrical aryl- and alkyl-disulphides are prepared from silylsulphides and thiosulphinates or thiosulphonates.Silyl sulphinic esters are also obtained in the reaction of the thiosulphonates.

PHOTOCHEMICAL TRANSFORMATION OF A DITHIOACETAL S-OXIDE INTO THE CORRESPONDING ALDEHYDE

Irradiation of an aldehyde dithioacetal S-oxide gives the corresponding aldehyde.The mechanism of this photochemical transformation is discussed and its application to organic synthesis is also described.

The Reaction of Ph3P+SR with Thiols: A Simple, Efficient Synthesis of Unsymmetrical Disulphides

Reaction of Ph3P+SRClO4-, prepared electrochemically from RSSR and Ph3P, with thiols in n-hexane at room temperature gave unsymmetrical disulphides in excellent yields with recovery of Ph3P.