69187-12-8

Upstream product

• 129972-74-3 C₂₈H₃₆O₆PS⁽¹⁺⁾*I^(1-) 
• 106-45-6 para-thiocresol 
• 109-79-5 n-butanethiol 
• 629-45-8 dibutyl disulfide 
• 103-19-5 di(p-tolyl) disulfide 
• 2757-37-1 didodecyl disulfide 
• 2550-40-5 1,2-dicyclohexyl disulfide 
• 5335-87-5 4,4'-dimethoxyphenyl disulfide 
• 882-33-7 diphenyldisulfane 
• 20129-23-1 butyl phenyl disulfide 
• 29627-28-9 4-methylphenyl cyclohexyl disulfide 
• 735269-14-4 1-cyclohexyl-2-(4-methoxyphenyl)disulfane 
• 83180-92-1 1-(4-methylphenyldisulfanyl)-4-methoxybenzene 
• 2943-42-2 di(4-methyl)phenylthiosulfonate 

Relevant academic research and scientific papers

PdCl2/DMSO-Catalyzed Thiol-Disulfide Exchange: Synthesis of Unsymmetrical Disulfide

Unsymmetrical disulfides have been effectively prepared through thiol exchange with symmetrical disulfides employing a simple PdCl2/DMSO catalytic system. The given method features excellent functional group tolerance, a broad substrate scope, and operational simplicity. This reaction is especially useful for late-stage functionalization of bioactive scaffolds such as peptides and pharmaceuticals. Disulfide-containing organic dyes have also been prepared. This transformation could be extended to thiol-diselenide or thiol-ditelluride exchange affording RS-SeR′ or RS-TeR′.

Alternating Current Electrolysis for the Electrocatalytic Synthesis of Mixed Disulfide via Sulfur–Sulfur Bond Metathesis towards Dynamic Disulfide Libraries

A novel approach of electrolysis using alternating current was applied in the sulfur–sulfur bond metathesis of symmetrical disulfides towards unsymmetrical disulfides. As initially expected, a statistical distribution in disulfides was obtained. Furthermore, the influence of electrode polarisation by alternating current was investigated on a two-disulfide matrix. The highly dynamic nature of this chemistry resulted in the creation of dynamic disulfide libraries by expansion of the matrices, consisting of up to six symmetrical disulfides. In addition, mixing of matrices and stepwise expanding of a matrix by using alternating current electrolysis were realised.

Thiolation of Pyridine-2-sulfonamides using Magnesium Thiolates

The thiolation of pyridine-2-sulfonamides using magnesium thiolates is reported. The ortho-functionalizations of these sulfonamides using TMPMgCl·LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed by electrophilic quenching produced a range of 3-functiona

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.

One-pot synthesis of unsymmetrical disulfides using 1-chlorobenzotriazole as oxidant: Interception of the sulfenyl chloride intermediate

A high-yielding and low temperature one-pot procedure is described for unsymmetrical disulfide synthesis from two different thiols using 1-chlorobenzotriazole (BtCl) as oxidant. The mechanism of the coupling involves in situ trapping of the sulfenyl chloride intermediate R1SCl by nucleophilic benzotriazole (BtH) to form R1SBt, which protects R1SCl from forming the homodimer R1SSR1. The methodology is applicable to all types of thiol (aliphatic, aromatic, heteroaromatic), with a variation developed for aliphatic-aliphatic couplings. Differentially N-protected cysteines couple to afford the unsymmetrical cystine derivatives in high yield (90%), which serves as a model for the one-pot intermolecular coupling of cysteine-containing peptides to form peptide disulfide heterodimers. Minimal exchange in aromatic-aromatic disulfide synthesis is noted on account of the mild conditions.

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.

PHOTOCHEMICAL REDUCTION OF N-TOSYLSULFILIMINES WITH THIOLATE ANION

The reaction between N-tosyldiarylsulfilimines and p-toluenethiolate anion did not take place in the dark even upon heating up to 62o but proceeded smoothly upon irradiation with visible light in DMF at room temperature, affording S-N bond cleavage products.

FACILE REDUCTION OF SULFINIC ACID TO DISULFIDE WITH THIOL AND CHLOROTRIMETHYLSILANE

Sulfinic acids were found to be readily reduced to the corresponding disulfide quantitatively at room temperature upon treatment with a mixture of thiols and chlorotrimethylsilane.