2943-20-6

Upstream product

• 68048-41-9 tert-Butyl thionitrate 
• 930-69-8 sodium thiophenolate 
• 14204-27-4 N-phenylthiophthalimide 
• 75-66-1 2-methylpropan-2-thiol 
• 64168-52-1 4'-nitrobenzenesulfenanilide 
• 108-98-5 thiophenol 
• 16079-15-5 phenylsulfanylium 
• 13071-79-9 terbufos 
• 33704-41-5 N-(tert-butyldisulfide)phthalimide 
• 98-80-6 phenylboronic acid 
• 62-53-3 aniline 
• 150-60-7 dibenzyl disulphide 
• 77329-76-1 (S)-t-butyl-p-toluenethiosulfinate 
• 931-59-9 benzenesulfenyl chloride 

Downstream Products

• 63752-74-9 S-tert-butyl benzenesulfinothioate 
• 89523-59-1 S-phenyl 2-methylpropane-2-sulfinothioate 

Relevant academic research and scientific papers

Sandmeyer-Type Reductive Disulfuration of Anilines

A transition metal/ligand-free disulfuration of anilines with disulfur transfer reagents (dithiosulfonate or tetrasulfide) is reported herein. The reaction, which can be considered as a reductive disulfuration variation of the classic Sandmeyer reaction, is performed under mild conditions and exhibits broad scope across the aniline substrate and disulfur transfer reagent classes. The gram-scale synthesis of disulfides is successfully achieved through this method, rendering the approach highly valuable.

Directed oxidative coupling of thiols in the synthesis of unsymmetrical disulfides

Oxidative coupling of two different thiols bearing aliphatic, alicyclic, aromatic, and hetero-aromatic moieties promoted by mild oxidizing agents, viz., sterically hindered o-benzo(imino)-quinones, carried out in N-methylpyrrolidone at room temperature led to unsymmetrical disulfides. Among the studied oxidizers, the most active was 3,6-di-tert-butyl-o-benzoquinone, which, in contrast to 3,5-di-tert-butyl-o-benzoquinone, was not involved in the Michael addition. Under the optimal reaction conditions, the yields of the target unsymmetrical disulfides reach 81%.

Phthalimide-Carried Disulfur Transfer to Synthesize Unsymmetrical Disulfanes via Copper Catalysis

A versatile Cu-catalyzed cross-coupling reaction to various unsymmetrical disulfanes has been presented, from phthalimide-carried disulfur transfer reagents and commercially available boronic acids under mild and practical conditions. The method features the unprecedented use of phthalimide-carried disulfurating reagents (Harpp reagent) in cross-coupling chemistry and is highlighted by the broad substrate scopes, even applicable for the transfer of aryl-disulfur moieties (ArSS-). Notably, the robustness of this methodology is shown by the late-stage modification of bioactive scaffolds of coumarin, estrone, and captopril.

Electro-Oxidative S?H/S?H Cross-Coupling with Hydrogen Evolution: Facile Access to Unsymmetrical Disulfides

Sulfur is an essential element because it exists widely in proteins. The disulfide bond is an important moiety in many different types of significant organic molecules. A new approach for oxidant- and catalyst-free S?H/S?H cross-coupling, with hydrogen ev

Nucleophilic reactions of phorate and terbufos with reduced sulfur species under anoxic conditions

The reactions of phorate and terbufos with bisulfide (HS-), polysulfide (Sn2-), thiosulfate (S2O 32-), and thiophenolate (PhS-) were examined in well-defined aqueous solution under anoxic conditions to investigate their role in the degradations of phorate and terbufos. Reactions were monitored at various concentrations of reduced sulfur species to obtain the second-order rate constants. The reactivity of the reduced sulfur species decreased in the order Sn2- > PhS- > HS- > S 2O32-. Hydrolysis products, formaldehyde and diethyl disulfide/di-tert-butyl disulfide, indicated that OH-/H 2O attacked the carbon atom between the two sulfur atoms, the so-called thioacetal carbon, which is very reactive due to the presence of the two neighboring sulfur atoms. The reaction of phorate and terbufos with PhS - was investigated to study the transformation products in the reactions with reduced sulfur species. The transformation products demonstrated that the observed increase in rate constants in the reaction with reduced sulfur species compared to hydrolysis could result from the nucleophilic attack of reduced sulfur species at the α-carbon of the ethoxy group and at the thioacetal carbon atom. The temperature dependence of measured second-order rate constants of the reaction of phorate and terbufos with HS- over 25-50°C was investigated to explore activation parameters, which are not significantly different for phorate and terbufos. All of the observations may imply similar pathways in the degradation of phorate and terbufos in the presence of reduced sulfur species. Slightly higher hydrolysis rates of terbufos and second-order reaction rate constants for the reactions with sulfur species of terbufos compared with those for phorate are observed, which could be attributed to the slightly different substituents.

A new electrochemical method of preparation of unsymmetrical disulfides

A new method is described for the preparation of unsymmetrical disulfides by reaction of the electrogenerated sulfenium cation R1-S+ with thiols or disulfides.

The 'Thio-Arbuzov' reaction of sulfenate esters with sulfenyl chlorides: Fate of the thiosulfinate product

The further reaction of thiosulfinate esters (putative products of the 'Thio-Arbuzov' reaction of sulfenate esters with sulfenyl chlorides) with sulfenyl chlorides and sulfenate esters has been studied. In the former case, sulfinyl chlorides and disulfides are formed. In the latter case sulfinate esters and disulfides are obtained. Copyright (C) 1996 Elsevier Science Ltd.

Sodium Tellurite as a Mild and Selective Oxidizing Agent for Thiols: Its Use in the One-Pot Synthesis of Unsymmetrical Disulfides

Sodium tellurite acts as a mild and highly selective oxidizing agent for thiols under phase-transfer conditions at room temperature.Aromatic and benzylic thiols are rapidly converted to disulfides.Short-chain primary thiols undergo oxidation in preference to long-chain thiols.Secondary thiols are sluggish in oxidation and tertiary thiols remain intact.No overoxidation of the sulfur atom is observed.Similar results are also obtained with sodium tellurate.

4'-NITROARENESULPHENANILIDES: THEIR USE IN THE SYNTHESIS OF UNSYMMETRICAL DISULPHIDES

The reaction of 4'-nitroarenesulphenanilides with thiols in the presence of boron trifluoride etherate can provide an effective route to unsymmetrical disulphides.

CATALYTIC OXIDATION OF THIOLS BY COENZYME PQQ

Oxidation of thiols by coenzyme PQQ as a new enzymatic oxidation-reduction model was found to proceed catalytically under aerobic conditions to give corresponding disulfides.