39153-60-1

Upstream product

• 59057-35-1 2,4,6-trimethylbenzenesulphinic acid 
• 39153-67-8 Bis-mesitylsulfonyl-methan 
• 108-67-8 1,3,5-trimethyl-benzene 
• 16182-15-3 2,4,6-trimethylbenzenesulfonohydrazide 
• 39153-66-7 bis(2,4,6-trimethylphenylthio)methane 
• 1541-10-2 mesitylthiol 
• 773-64-8 2-mesitylenesulphonyl chloride 

Downstream Products

• 1483-92-7 bis(2,4,6-trimethylphenyl)disulfide 
• 1452822-42-2 mesityl(1,1,2,2-tetrafluoro-3-(4'-(hexyloxy)biphenyl-4-yl)propyl)sulfane 
• 42085-98-3 (2,4-dinitro-phenyl)-mesityl sulfone 

Relevant academic research and scientific papers

Dual Roles of Rongalite: Reductive Coupling Reaction to Construct Thiosulfonates Using Sulfonyl Hydrazides

A tunable and practical transformation of structurally diverse sulfonyl hydrazides into thiosulfonates in the presence of Rongalite (NaHSO 2·CH 2O) was developed. Transition-metal-free conditions, operational simplicity, and readily available reagents are the striking features of this protocol. It is the first example for the synthesis of thiosulfonates using sulfonyl hydrazides with the assistance of reductant. Additionally, the mechanistic studies revealed that this transformation probably undergoes via a reducing-coupling pathway.

Direct conversion of sulfinamides to thiosulfonates without the use of additional redox agents under metal-free conditions

Direct conversion of sulfinamides to thiosulfonates is described. Without the use of additional redox agents, the reaction proceeds smoothly in the presence of TFA under metal-free conditions. This protocol possesses many advantages such as odourless and stable starting materials, broad substrate scope, selective synthesis, and mild reaction conditions. This journal is

Synthesis of symmetrical / unsymmetrical thiosulfonates through the disproportionate coupling reaction of sulfonyl hydrazide mediated by phosphomolybdic acid

Phosphomolybdic acid (H3PMo12O40) is reported as a green low-cost catalyst for the synthesis of symmetrical / unsymmetrical thiosulfonates via the disproportionate coupling reaction of sulfonyl hydrazide. The attributes of this reported catalytic system include low catalyst loadings (1 mol%), efficient turnover, and high yields (up to 94%). Additionally, this reaction mechanism involves the formation of a thiyl radical and sulfonyl radical via sulfinyl radical disproportionation.

CuCl2-promoted decomposition of sulfonyl hydrazides for the synthesis of thiosulfonates

Sulfonyl hydrazides recently received much attention as reagents for the introduction of sulfur-containing functional groups into organic compounds, because both sulfonyl and sulfenyl sources could be generated by the oxidation and decomposition of the sulfonyl hydrazides, respectively. However, the transformations of sulfonyl hydrazides into thiosulfonates, which could be produced by the reaction between sulfonyl and sulfenyl sources, have been less investigated. In this manuscript, we describe CuCl2-promoted selective synthesis of thiosulfonates from sulfonyl hydrazides. A variety of thiosulfonates were produced in moderate to good yields. The mechanism involving radical intermediates such as sulfonyl radical and thiyl radical was proposed on the basis of the previously reported references and mechanistic investigations. In addition, quantum chemical simulations revealed that Cu-promoted decomposition of sulfonyl hydrazides is thermodynamically viable in the developed conditions.

Preparation method of thiosulfonate compounds in aqueous phase

The invention relates to a preparation method of thiosulfonate compounds in an aqueous phase. The preparation method comprises adding sulfonyl hydrazide, an accelerant, an oxidant and solvent water into a Schlenk reaction bottle, stirring to allow to react under certain temperature and air atmosphere, and carrying out free radical coupling reaction to obtain the thiosulfonate compounds.

Transition-Metal-Free Synthesis of Thiosulfonates through Radical Coupling Reaction

An efficient and practical transition-metal-free radical coupling reaction of sulfonyl hydrazides mediated by NIS/K 2 S 2 O 8 has been developed to afford a variety of biological activity thiosulfonates in moderate to excellent yields. Compared to a known approach for the synthesis of thiosulfonates from sulfonyl hydrazides, this strategy features high yields, mild reaction conditions, and broad substrate scope. The mechanistic studies revealed that the procedure undergoes via a radical cross-coupling process for the construction of S-S bonds.

Visible light induced decomposition of sulfonyl hydrazides using Pd/ZrO2nanocomposite photocatalyst

A new approach to synthesis of thiosulfonates has been developed under mild conditions without any oxidants and promoting reagents through a Pd/ZrO2nanocomposite photocatalyst catalyzed decomposition of sulfonyl hydrazides. This protocol gave the products in moderate yields, comparable to the best results reported so far. Finally, a plausible reaction mechanism was proposed.

Tunable and Practical Synthesis of Thiosulfonates and Disulfides from Sulfonyl Chlorides in the Presence of Tetrabutylammonium Iodide

A tunable and practical synthesis of electrophilic sulfenylating reagents, thiosulfonates and disulfides, from inexpensive and easily available sulfonyl chlorides, has been developed. By appropriate choice of solvents, the reaction of sulfonyl chlorides and tetrabutylammonium iodide gave the target products in good to excellent yields, respectively. These transformations probably proceed through a reducing–coupling pathway. (Figure presented.).

STRUCTURE AND CONFORMATION OF SYMMETRIC ARYL THIOSULPHONIC ESTERS

The symmetric thiosulphonic esters R-SO2-S-R (R = CH3, C6H5, p-CH3-C6H4, p-CH3O-C6H4, p-Cl-C6H4, 2,4,6-(CH3)3-C6H2, 2,4,6-(i-C3H7)3-C6H2) have been prepared by a one-step synthesis partially reducing the sulphonyl chlorides with KI in the presence of catalytic amounts of pyridine.The crystal structures of the aryl derivatives X-C6H4-SO2-S-C6H4-X (X = H, CH3, Cl) have been determined using single crystal X-ray diffractometric data: C6H5-SO2-S-C6H5 (MoKα): P2/n, a = 12.413(4), b = 8.537(2), c = 12.649(5) Angstroem, β = 116.50(2) deg, Z = 4, final R = 0.0485; CH3-C6H4-SO2-S-C6H4-CH3 (CuKα): P21/n, a = 13.932(6), b = 12.076(6), c = 8.326(4) Angstroem, β = 93.40(6) deg, Z = 4, final R = 0.0425; Cl-C6H4-SO2-S-C6H4-Cl (MoKα): P21/n, a = 13.716(9), b = 11.932(8), c = 8.206(4) Angstroem, β = 92.47(2) deg, Z = 4, final R = 0.0493.The three structures are strictly similar with a conformation of the thiosulphonyl system essentially determined by the tendency of the non bonding electron pairs of S(II) to assume synclinal and antiperiplanar conformation with respect to the S(VI)-O bonds.The repulsion exerted by these pairs on the S(II)-C and S(II)-S(VI) bonding pairs justifies the narrowing of the S(VI)-S(II)-C angle with respect to the tetrahedral value.Electronic effects due to the para substituents in the phenyl rings superimpose that repulsion producing a different narrowing in the three derivatives.These effects influence also the S(VI)-S(II) distance which is shorter in the case of X = H, where the angle S(VI)-S(II)-C is larger.The angular deformations of the environment of S(VI) make the two oxygen atoms non equivalent, so that S(VI) is chiral.