4837-39-2

Upstream product

• 2550-40-5 1,2-dicyclohexyl disulfide 
• 5675-01-4 cyclohexanesulfinic acid 
• 1569-69-3 Cyclohexanethiol 
• 110-82-7 cyclohexane 
• 136-01-6 cyclohexanecarboxylic acid Na-salt 
• 15459-94-6 S-nitrosocyclohexanethiol 

Downstream Products

• 368-42-3 cyclohexane-1-sulfonyl fluoride 
• 56717-64-7 pentafluorophenyl-cyclohexyl thioether 

Relevant academic research and scientific papers

Synthesis of Symmetrical and Unsymmetrical Thiosulfonates from Disulfides through Electrochemically Induced Disulfide Bond Metathesis and Site-Selective Oxidation

The anodic generation of symmetrical and unsymmetrical thiosulfonates is presented. First, the oxidation of disulfides yielding symmetrical thiosulfonates was realized. The direct synthesis is performed using a simple quasi-divided cell design, whereby using a supporting electrolyte is unnecessary. Its principle was then expanded to the conversion of unsymmetrical disulfides that were generated in situ through metathesis of two symmetrical disulfides. This enables a direct access to unsymmetrical thiosulfonates without any pre-functionalization or elaborate synthesis of the starting materials for the first time. The reaction scope was investigated by converting differently functionalized aliphatic and aromatic disulfides in moderate to very good yields. Furthermore, a sensitivity assessment for an improved reproducibility and a robustness screen to determine the compatibility of the reaction against functional groups were performed.

The organocatalytic synthesis of perfluorophenylsulfides: Via the thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates

The organic superbase t-Bu-P4-catalyzed direct thiolation of trimethyl(perfluorophenyl)silanes and thiosulfonates was developed. Yields of perfluorophenylsulfides of up to 97% under catalysis of 5 mol% t-Bu-P4 were achieved. This method was shown to provide an efficient way to construct the perfluorophenyl-sulfur bond under mild metal-free reaction conditions. This journal is

Synthesis method of alkyl thiosulfonate compound

The invention belongs to the technical field of synthesis of organic compounds, and provides a novel method for preparing an alkyl thiosulfonate compound. According to the method, under the conditions of acid and illumination, direct coupling of a sulfurous acid derivative and alkane is utilized to realize direct synthesis and preparation of the alkyl thiosulfonate compound. According to the method, a direct sulfo-substitution mode of alkane C-H bonds is adopted, reaction functional groups do not need to be configured in advance, conversion to the alkyl thiosulfonate compound is completed in one step, raw materials are cheap and easy to obtain, conditions are mild and green, operation is easy, convenient and safe, and the method has high economic prospects.

Nonheme iron-thiolate complexes as structural models of sulfoxide synthase active sites

Two mononuclear iron(ii)-thiolate complexes have been prepared that represent structural models of the nonheme iron enzymes EgtB and OvoA, which catalyze the O2-dependent formation of carbon-sulfur bonds in the biosynthesis of thiohistidine compounds. The series of Fe(ii) complexes reported here feature tripodal N4 chelates (LA and LB) that contain both pyridyl and imidazolyl donors (LA = (1H-imidazol-4-yl)-N,N-bis((pyridin-2-yl)methyl)methanamine; LB = N,N-bis((1-methylimidazol-2-yl)methyl)-2-pyridylmethylamine). Further coordination with monodentate aromatic or aliphatic thiolate ligands yielded the five-coordinate, high-spin Fe(ii) complexes [FeII(LA)(SMes)]BPh4 (1) and [FeII(LB)(SCy)]BPh4 (2), where SMes = 2,4,6-trimethylthiophenolate and SCy = cyclohexanethiolate. X-ray crystal structures revealed that 1 and 2 possess trigonal bipyramidal geometries formed by the N4S ligand set. In each case, the thiolate ligand is positioned cis to an imidazole donor, replicating the arrangement of Cys- and His-based substrates in the active site of EgtB. The geometric and electronic structures of 1 and 2 were analyzed with UV-vis absorption and M?ssbauer spectroscopies in tandem with density functional theory (DFT) calculations. Exposure of 1 and 2 to nitric oxide (NO) yielded six-coordinate FeNO adducts that were characterized with infrared and electron paramagnetic resonance (EPR) spectroscopies, confirming that these complexes are capable of binding diatomic molecules. Reaction of 1 and 2 with O2 causes oxidation of the thiolate ligands to disulfide products. The implications of these results for the development of functional models of EgtB and OvoA are discussed. This journal is

Iron(III)-Catalyzed Radical Cross-Coupling of Thiols with Sodium Sulfinates: A Facile Access to Thiosulfonates

A convenient and efficient synthesis of symmetrical and asymmetric thiosulfonates from thiols and sodium sulfinates is reported. The protocol involves iron(III)-catalyzed formation of sulfenyl and sulfonyl radicals in situ under aerobic conditions and their subsequent cross-coupling to afford thiosulfonates in 83-96% yield. The utilization of readily available, nontoxic, and inexpensive iron(III) as a catalyst and atmospheric oxygen as an oxidant is within the confines of green and sustainable chemistry.

Fast and efficient green synthesis of thiosulfonate S-esters by microwave-supported permanganate oxidation of symmetrical disulfides

Potassium permanganate absorbed on copper(II) sulfate pentahydrate has been found to be an efficient, inexpensive, and green oxidation agent for the synthesis of "symmetrical" thiosulfonate S-esters by oxidation of the corresponding symmetrical disulfides. The oxidation reactions were carried out under solvent-free reaction conditions within 15 min under the influence of microwave irradiation, as well as (for comparison) supported by conventional heating, to afford yields of the thiosulfonate S-esters in the range of 60-83%. The oxidation reaction appears to proceed (at least partly) via an intermediate symmetrical vic-disulfoxide.

Facile synthesis of symmetric thiosulfonates by oxidation of disulfide with oxone/MX (MX = KBr, KCl, NaBr and NaCl)

Abstract A new method is described for the oxidation of aliphatic- and aromatic disulfides containing electron-donating and electron-withdrawing groups to their corresponding thiosulfonates using oxone in combination with the MX (MX = KBr, KCl, NaBr and NaCl). No obvious electronic effects influence the yields of thiosulfonates. Avoiding the usage of toxic and unstable reagents, mild reaction conditions, short reaction times and cost-effectiveness are advantages of this methodology when likened to known methods for thiosulfonates syntheses.

Synthesis of sulfonyl chlorides and thiosulfonates from H2O 2-TiCl4

A new method is described for the oxidative chlorination of thiols to sulfonyl chlorides using titanium tetrachloride in combination with the oxidant hydrogen peroxide. Direct conversion of thiols into their corresponding thiosulfonates is also reported. Good to excellent yields, short reaction times, high efficiencies, cost-effectiveness, and, facile isolation of the desired products make the present methodology a practical alternative.

Zinc dichromate trihydrate (ZnCrmiddot;3H) as an efficient reagent for the one-pot synthesis of thiosulfonates from thiols

ZnCrH is a readily available and efficient reagent for the one-pot synthesis of a variety of thiosulfonates by chemoselective oxidation of thiols. Georg Thieme Verlag Stuttgart New York.

Dinitrogen tetroxide impregnated charcoal (N2O 4/Charcoal): Selective oxidation of thiols to disulfides or thiosulfonates

Selective oxidation of thiols to disulfides (RSSR) was performed by using catalytic amounts of dinitrogen tetroxide/charcoal in chloroform at r.t. while the reaction of thiols with four molar equivalents of the reagent in dichloromethane afforded thiosulfonates (RSO2SR) with excellent yields. Copyright Taylor & Francis Group, LLC.