16601-16-4

Upstream product

• 150-60-7 dibenzyl disulphide 
• 629-45-8 dibutyl disulfide 
• 109-79-5 n-butanethiol 
• 114657-01-1 5-(n-butylthio)-1,3-dimethyl-5-(4'-methoxybenzyl)barbituric acid 
• 100-53-8 phenylmethanethiol 
• 6493-73-8 dibenzyltrisulfide 
• 4991-51-9 bis(p-tolyl) trisulfide 
• 23670-27-1 Sodium; phenyl-methanethiosulfonate 
• 16642-95-8 butanesulfinic acid sodium salt 
• 6313-36-6 benzyl thiosulphate 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 2943-26-2 S-benzyl O-ethylxanthate 
• 26726-20-5 sodium n-butylsulfanesulfonate 

Downstream Products

• 16599-29-4 Phenylmethanthiosulfinsaeure-butylester 
• 93247-11-1 C₁₁H₁₆OS₂ 

Relevant academic research and scientific papers

Rhodium-catalyzed disulfide exchange reaction

A system of RhH(PPh3)4, trifluoromethanesulfonic acid, and (p-tol)3P catalyzes the disulfide exchange reaction. Treatment of two symmetrical dialkyl disulfides with the catalyst provides an equilibrium mixture of three dis

Phosphine-free cationic rhodium(I) complex-catalyzed disulfide exchange reaction: Convenient synthesis of unsymmetrical disulfides

A phosphine-free cationic rhodium(I) complex, [Rh(cod)2]BF 4, is an effective catalyst for disulfide exchange reaction of symmetrical disulfides to unsymmetrical disulfides under inert atmosphere. This reaction could be carried out u

NFSI-catalyzed S[sbnd]S bond exchange reaction for the synthesis of unsymmetrical disulfides

The metal-free S[sbnd]S bond exchange reaction of symmetrical disulfides catalyzed by NFSI is described. This novel protocol provides a facile and efficient approach to accessing important unsymmetrical disulfides. Furthermore, this strategy could also be utilized in the late-stage functionalization of amino acids, drugs, and natural products. The broad substrate scope, good functional group tolerance and easy accessibility of catalyst indicate that this strategy affords a green and practical complementary method to various unsymmetrical disulfides.

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

An efficient and new method for the synthesis of disulfides and sulfides via the reaction of aryl halides with ethyl potassium xanthogenate in the presence of MOF-199 is described. O -Ethyl- S -aryl carbonodithioate has a key role as an intermediate in this procedure; it was converted into symmetrical diaryl disulfides in DMF. Additionally, this could be applied to the synthesis of unsymmetrical aryl alkyl(aryl′) disulfides by the reaction with S -alkyl(aryl) sulfurothioates (Bunte salts) as well as unsymmetrical aryl alkyl(aryl′) sulfides in DMSO.

Aryl-aryl, aryl-alkyl, alkyl-alkyl asymmetric the sulfur compounds and its synthetic method

The invention discloses a synthesis method of aryl-aryl, aryl-alkyl and alkyl-alkyl asymmetric persulfides as shown in a formula (II) or a formula (IV). According to the synthesis method, with sulfinic acid sodium salt, and halogenated hydrocarbon and Na2S2O3 as reaction materials or Bunte salt as a reaction material instead of the halogenated hydrocarbon and Na2S2O3, the aryl-aryl, aryl-alkyl and alkyl-alkyl asymmetric persulfides are obtained by reaction in the absence of transition metal. The synthesis method has the advantages that the reaction is efficient; the yield is high; a vulcanizing reagent is cheap, easily available, stable, and free of pungent smell; no strong acid or alkali or extra oxidizing or reducing agent is added in reaction; the condition is relatively mild; and no transition metal is used as a catalyst in the reaction, and therefore the method is economical, practical and friendly to the environment; a reaction substrate is easy to prepare; the reaction efficiency is high after the reaction is amplified, and therefore, the synthesis method has a wide application prospect and practical value.

Transition-metal-free persulfuration to construct unsymmetrical disulfides and mechanistic study of the sulfur redox process

A sulfur redox process has been developed between sulfinate and thiosulfate, which efficiently affords diverse unsymmetrical disulfides and provides a new method to modify pharmaceuticals and natural products without requiring an extra oxidant or reductant. Gram-scale investigation further demonstrates the practicality and application potential of this process. Isolated key intermediates and a series of control experiments afford an unusual process, which reveals the mechanism of comproportionation and the transition-metal-free sulfur redox process.

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.

OXIDATION OF THIOL WITH 5-ARYLIDENE-1,3-DIMETHYLBARBITURIC ACID: APPLICATION TO SYNTHESIS OF UNSYMMETRICAL DISULFIDE

5-Arylidene-1,3-dimethylbarbituric acid derivatives, such as 1a and 1b, effectively oxidized both alkane- and benzenethiols to disulfides under neutral condition with concomitant formation of the dihydro compounds (2a) and (2b).Thiol adduct of the dihydro compound was prepared as a stable compound and successfully applied to the synthesis of unsymmetrical disulfide under mild condition in excellent yield.Mechanistic consideration for the oxidation was also described briefly.

OXIDATION OF THIOL BY 5-ARYLIDENE 1,3-DIMETHYLBARBITURIC ACID AND ITS APPLICATION TO SYNTHESIS OF UNSYMMETRICAL DISULFIDE

Oxidation of both aromatic and aliphatic thiols by 5-arylidene 1,3-dimethylbarbituric acid was found to proceed readily to give disulfides in good yield with concomitant reduction of the oxidant to the dihydro compound.Thiol adduct of the dihydro compound was succesfully applied to the synthesis of unsymmetrical disulfide under mild conditions in an excellent yield.