41424-41-3

Upstream product

• 64168-52-1 4'-nitrobenzenesulfenanilide 
• 536-74-3 phenylacetylene 
• 133957-59-2 2-(trimethylsilyl)ethyl benzenesulfenate 
• 882-33-7 diphenyldisulfane 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 931-59-9 benzenesulfenyl chloride 
• 128787-47-3 (E)-N-(4-nitrophenyl)-S-phenyl-S-<2-(phenylthio)-1-phenylvinyl>sulphimide 

Downstream Products

• 41424-40-2 (Z)-(1-phenylethene-1,2-diyl)bis(phenylsulfane) 

Relevant academic research and scientific papers

Solvent-Driven Mono- and Bis-sulfenylation of (E)-β-Iodovinyl Sulfones with Thiols for Flexible Synthesis of 1,2-Thiosulfonylalkenes and 1,2-Dithioalkenes

The nature of solvent is a key factor for stereoselective mono- and bis-thiolation of (E)-β-iodovinyl sulfones with thiols under basic conditions. A novel and unprecedented vicinal bisthiolation of (E)-β-iodovinyl sulfones with thiols under the influence of K2CO3/DMSO at room temperature for quick assembly of (E)-1,2-dithio-1-alkenes is presented. Solvent-induced stereoselective monosulfenylation of (E)-β-iodovinyl sulfones with thiols has also been established for the synthesis of both (E)- and (Z)-1,2-thiosulfonylethenes in MeCN and MeOH, respectively. Moreover, K2CO3-mediated desulfonylative-sulfenylation of (Z)-1,2-thiosulfonylethenes with thiols in DMSO furnished unsymmetrical (Z)-1,2-dithio-1-alkenes for the first time. The solvent-dependent versatile reactivity of (E)-β-iodovinyl sulfones has been successfully explored to provide a set of (E)-/(Z)-1,2-dithio-1-alkenes and (E)-/(Z)-1,2-thiosulfonyl-1-alkenes in good to high yields with excellent stereoselectivities. Notably, this operationally simple process utilizes a broad substrate scope with good functional group tolerance and compatibility. The efficacy of the process has been proven for gram-scale reactions, and plausible mechanistic models are outlined on the basis of experimental results and control experiments.

Hexafluoroisopropanol-Promoted Disulfidation and Diselenation of Alkyne, Alkene, and Allene

Hexafluoroisopropanol (HFIP)-promoted disulfidation and diselenation of C-C unsaturated bonds is reported. Reactions of unactivated alkyne, alkene, and allene, respectively, with disulfides or diselenides in HFIP led to desired products in good to excellent yields (up to 96percent). In contrast, other solvents, such as isopropanol and dichloroethane, could not promote the same reaction. This method revealed an example of HFIP-promoted transformations under the mild conditions, which greatly highlighted the unique reactivity of this special solvent.

CuI/glycerol mediated stereoselective synthesis of 1,2-bis-chalcogen alkenes from terminal alkynes: Synthesis of new antioxidants

(E)-1,2-Bis-chalcogen alkenes were stereoselectively prepared in good yields by the addition of diorganyl dichalcogenides to terminal alkynes using CuI/Zn/glycerol as a recyclable catalytic system. The antioxidant activity in vitro of four (E)-1,2-bis-cha

Bis-vinyl selenides obtained via iron(iii) catalyzed addition of PhSeSePh to alkynes: Synthesis and antinociceptive activity

In the present study the synthesis and antinociceptive activity of bis-vinyl selenides, prepared via FeCl3 promoted reaction addition of diorganyl dichalcogenides to alkynes, is described. The pharmacological results demonstrated that bis-vinyl selenides 3a, 3d, 3h and 3t elicited antinociceptive effect in the mouse formalin test. The antinociceptive effects of bis-vinyl selenides are not sensitive to electronic effects of the substituents on the aromatic ring directly bonded to the selenium atom. Bis-vinyl selenides 3h and 3t were the most promising molecules for pharmacological purposes since these bis-vinyl selenides were effective in both phases of the formalin test and against edema. A single dose of bis-vinyl selenides 3a, 3d, 3h and 3t did not cause acute toxicity in mice.

Disulfidation of Alkynes and Alkenes with Gallium Trichloride

(Matrix presented) Treatment of diphenyl disulfide and terminal alkynes with gallium trichloride afforded (E)-1,2-diphenylthio-1-alkenes selectively (E/Z > 20/1). Alkenes also underwent this reaction to form trans adducts.

Synthesis of 2-(Trimethylsilyl)ethyl Benzenesulfenate and Benzeneselenenate and Their Reaction with Some Electrophiles in the Presence of Tetrabutylammonium Fluoride

2-(Trimethylsilyl)ethyl benzenesulfenate was allowed to react with several halides in the presence of tetrabutylammonium fluoride (TBAF) to afford the corresponding phenyl sulfoxides as the main product.In the reaction of 2-(trimethylsilyl)ethyl benzeneselenenate and several halides with TBAF, the corresponding alcohols were obtained as the main product.

Boron Trifluoride-promoted Reaction of 4'-Nitrobenzenesulphenanilide with Alkynes. Formal Addition of Benzenesulphenyl Fluoride to Carbon-Carbon Triple Bonds

The BF3-promoted reaction of 4'-nitrobenzenesulphenanilide with simple alkyl- and aryl-alkynes at 80 deg C in the presence of tetrabutylammonium tetrafluoroborate provides a one-pot synthetic route to β-fluorovinyl sulphides via a formal regioselective and trans-stereospecific addition of benzenesulphenyl fluoride towards carbon-carbon triple bonds.

ELECTROPHILIC ADDITION OF 4'-NITROBENZENESULPHENANILIDE TO ALKYNES, EFFECTS OF ARYL AND ALKYL SUBSTITUENTS AT RING CARBONS OF INTERMEDIATE THIIRENIUM IONS

The BF3-promoted addition of 4'-nitrobenzenesulphenanilide, NBSA, to a number of aryl- and alkyl-acetylenes has been investigated in dichloromethane, p-xylene and/or benzene.Diphenylacetylene, 1a, 1-phenylbutyne, 1b, and 1-phenylpropyne, 1c, generally lead to 1,2-bis(phenylthio)alkenes 4a-c, and N-(4-nitrophenyl)-S-phenyl-S-(2-phenylthiovinyl)sulphimides, 6a-c, in fair to good yields with trans stereospecificity.Phenylacetylene, 1d, similarly gives the corresponding bis(phenylthio)adduct 4d and sulphimide 6d in dichloromethane, but in the aromatic solvents these products are essentially suppressed in favour of 1-aryl-1-phenyl-2-(phenylthio)ethylenes 7d.On the other hand, alkyl- and, particularly, dialkyl-substituted acetylenes preferentially afford β-fluorovinyl sulphides, 5, with trans stereospecifity.These findings are interpreted in terms of a different reactivity towards nucleophilic attack of the intermediate aryl- and alkyl-trihirenium ions which would result from electrophilic sulphenylation of the corresponding alkynes.Steric effects of the substituents are believed to play a major role in determining the different reactivity observed.