22582-35-0

Upstream product

• 4108-56-9 Prop-2-ynylsulfanylmethyl-benzene 
• 85143-01-7 5-Benzylsulfanyl-4-methyl-[1,2,3]selenadiazole 
• 3012-37-1 benzyl thiocyanate 
• 4529-04-8 1-propynyl lithium 
• 16601-02-8 S-benzyl 4-methylbenzenethiosulfonate 
• 100-53-8 phenylmethanethiol 
• 3492-64-6 sodium benzylmercaptide 
• 590-14-7 1-bromo-1-propene 
• 150-60-7 dibenzyl disulphide 
• 78-88-6 2,3-Dichloroprop-1-ene 
• 164529-26-4 2-chloro-3-benzylsulfanyl-1-propene 
• 85143-16-4 benzylsulfanyl-acetone semicarbazone 

Downstream Products

• 25558-03-6 benzyl 1-propynyl sulfone 
• 52755-44-9 (E)-1-(benzylthio)-1-propene 
• 1393561-73-3 [(2-methylhexylsulfonyl)methyl]benzene 
• 1393559-85-7 (E)-[(2-methylhex-1-enylsulfonyl)methyl]benzene 
• 1393560-93-4 (E)-benzyl(2-methylhex-1-enyl)sulfane 

Relevant academic research and scientific papers

Dehydrochlorination of 2-chloroprop-2-en-1-yl sulfides

Dehydrochlorination of 2-chloroprop-2-en-1-yl sulfides on heating with solid potassium hydroxide afforded the corresponding 1-(organylsulfanyl)propynes in moderate to high yields and minor isomeric allene derivatives, organylsulfanylpropadienes.

Alkynylation of Thiols with Ethynylbenziodoxolone (EBX) Reagents: α- Or β- π-Addition?

The alkynylation of thiols with EthynylBenziodoXolone (EBX) reagents is a fast and chemoselective method for the synthesis of thioalkynes. Combined experimental and computational studies are reported, which led to the identification of a new mechanism for

Divergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor–Acceptor Cyclopropanes

Efficient methods for the convergent synthesis of (poly)cyclic scaffolds are urgently needed in synthetic and medicinal chemistry. Herein, we describe new annulation reactions of thioalkynes with phthalimide-substituted donor–acceptor cyclopropanes, which gave access to highly substituted cyclopentenes and polycyclic ring systems. With silyl-thioalkynes, the Lewis acid catalyzed [3+2] annulation reaction with donor–acceptor cyclopropanes took place to afford 1-thio-cyclopenten-3-amines. On the other hand, an unprecedented polycyclic compound was formed with alkyl-thioalkynes through a reaction pathway directly involving the phthalimide group. The two transformations proceeded in good yields and tolerated a large variety of functional groups.

Fast and highly chemoselective alkynylation of thiols with hypervalent iodine reagents enabled through a low energy barrier concerted mechanism

Among all functional groups, alkynes occupy a privileged position in synthetic and medicinal chemistry, chemical biology, and materials science. Thioalkynes, in particular, are highly useful, as they combine the enhanced reactivity of the triple bond with a sulfur atom frequently encountered in bioactive compounds and materials. Nevertheless, general methods to access these compounds are lacking. In this article, we describe the mechanism and full scope of the alkynylation of thiols using ethynyl benziodoxolone (EBX) hypervalent iodine reagents. Computations led to the discovery of a new, three-atom concerted transition state with a very low energy barrier, which rationalizes the high reaction rate. On the basis of this result, the scope of the reaction was extended to the synthesis of aryl- and alkyl-substituted alkynes containing a broad range of functional groups. New sulfur nucleophiles such as thioglycosides, thioacids, and sodium hydrogen sulfide were also alkynylated successfully to lead to the most general and practical method yet reported for the synthesis of thioalkynes.

Specific features of the reactions of 2,3-dichloro-1-propene with dibenzylchalcogenides in the system hydrazine hydrate-alkali

Dibenzyldisulfide and -diselenide react with 2,3-dichloro-1-propene in the system hydrazine hydrate-KOH by the domino mechanism: nucleophilic substitution of the allyl chlorine, dehydrochlorination with participation of the chlorine atom at the sp 2

Synthetic scope, computational chemistry and mechanism of a base induced 5-endo cyclization of benzyl alkynyl sulfides

We present an experimental and computational study of the reaction of aryl substituted benzyl 1-alkynyl sulfides with potassium alkoxide in acetonitrile, which produces 2-aryl 2,3-dihydrothiophenes in poor to good yields. The cyclization is most efficient with electron withdrawing groups on the aromatic ring. Evidence indicates there is rapid exchange of protons and tautomerism of the alkynyl unit prior to cyclization. Theoretical calculations were also conducted to help rationalize the base induced 5-endo cyclization of benzyl 1-propynyl sulfide (1a). The potential energy surface was calculated for the formation of 2,3-dihydrothiophene in a reaction of benzyl 1-propynyl sulfide (1a) with potassium methoxide. Geometries were optimized with CAM-B3LYP/6-311+G(d,p) in acetonitrile with the CPCM solvent model. It is significant that the benzyl propa-1,2-dien-1-yl sulfane (6) possessed a lower benzylic proton affinity than the benzyl prop-2-yn-1-yl sulfane (8) thus favoring the base induced reaction of the former. From benzyl(propa-1,2-dien-1- yl sulfane (6), 2,3-dihydrothiophene can be formed via a conjugate base that undergoes 5-endo-trig cyclization followed by a protonation step.

A new approach to the synthesis of 2-vinylthiophenes and selenophenes; competition between free radical and anionic cycloaromatization of bridged di- and tetrapropargylic sulfides and selenides

A series of unknown di- and tetrapropargylic sulfides and selenides have been prepared. In the presence of t-BuOK in dry THF these compounds underwent isomerization to the corresponding diallenes, followed by a tandem anionic cyclization and aromatization

A novel base-induced cyclization of selected benzyl alkynyl sulfides for the synthesis of 2-aryl-2,3-dihydrothiophenes

2-Halobenzyl 1-alkynyl sulfides undergo an unprecedented dihydrothiophene formation when treated with 2 equiv. of KOtBu in CH3CN. The reaction, believed to proceed via a 5-endo-dig cyclization, is sluggish or non-existent in the absence of the halogen. (C) 2000 Elsevier Science Ltd.

Selenium Heterocycles. XXXV. Synthesis and Pyrolysis of Aryloxy-, Arylthio-, and Arylseleno-1,2,3-selenadiazoles

A series of 4-substituted-5-arylthio-1,2,3-selenadiazoles, 4-substituted-5-arylseleno-1,2,3-selenadiazoles and 4-aryloxymethyl-1,2,3-selenadiazoles were synthesized.Pyrolysis of these compounds afforded the corresponding acetylenes XI, XIII (X = S, Se) and XII, respectively.Oxidation of 4-substituted-5-arylthio-1,2,3-selenadiazoles (XIV) with m-chloroperbenzoic acid gave 4-substituted-5-arylsulfinyl-1,2,3-selenadiazoles (XV) and 4-substituted-5-arylsulfonyl-1,2,3-selenadiazoles (XVI).