75717-41-8

Upstream product

• 13910-16-2 n-octylsulfanylbenzene 
• 42843-49-2 (Z)-1-bromo-1-octene 
• 51751-87-2 (E)-1-bromo-1-octene 
• 17314-33-9 tributyltin phenyl sulfide 
• 30506-39-9 phenyl 1-octyl sulfoxide 
• 121410-98-8 O-<1,1-bis(phenylthio)methylheptyl> S-methyl dithiocarbonate 
• 87514-05-4 Trimethyl-((Z)-1-phenylsulfanyl-oct-1-enyl)-silane 
• 629-05-0 n-octyne 
• 108-98-5 thiophenol 
• 52356-93-1 (Z)-1-octenyl iodide 
• 111-71-7 heptanal 
• 882-33-7 diphenyldisulfane 
• 3561-67-9 bis(phenylthio)methane 

Downstream Products

• 132618-05-4 (+/-)_S-(Z)-1-(phenylsulfinyl)oct-1-ene 
• 111-65-9 octane 
• 111-66-0 oct-1-ene 

Relevant academic research and scientific papers

Synthesis of vinyl sulfides under base-free conditions using selenium ionic liquid

A very simple procedure is described for the efficient synthesis of vinyl sulfides by hydrothiolation of terminal alkynes using 1-n-butyl-3- methylimidazolium methylselenite, [bmim][SeO2(OCH3)]. The reaction proceeds cleanly under mi

Alkyne hydrothiolation catalyzed by a dichlorobis(aminophosphine) complex of palladium: Selective formation of cis-configured vinyl thioethers

Cis all round: Dichlorobis[1-(dicyclohexylphosphanyl)piperidine]palladium, [(P{(NC5H10)(C6H11) 2})2Pd(Cl)2], is a highly efficient alkyne hydrothiolation catalyst and the first generally applicable system that selectively generates cis-configured anti-Markovnikov adducts in excellent yields within only a few minutes at 120 °C in the presence of only 0.05 mol % of the catalyst (see scheme).

Water-promoted regioselective hydrothiolation of alkynes

Water promotes hydrothiolation of unactivated alkynes efficiently without any catalyst or additive. The reaction at room temperature furnishes vinyl sulfides with high regioselectivity via anti-Markovnikov addition. The terminal al- kynes provide dithiola

Reductive addition of the benzenethiyl radical to alkynes by amine-mediated single electron transfer reaction to diphenyl disulfide

Hydrothiolation of alkynes proceeds with diphenyl disulfide and tripropylamine. Amine-mediated single electron transfer to diphenyl disulfide can be proposed for the reaction mechanism. Applications of the method to radical cyclizations of eneyne compound

Stereoselective preparation of functionalized acyclic alkenylmagnesium reagents using i-PrMgCl-LiCl

(Chemical Equation Presented) Acyclic functionalized alkenyl iodides are converted with high stereoselectivity to the corresponding functionalized alkenylmagnesium derivatives by the reaction with i-PrMgCl-LiCl between -40 and -20°C. Functional groups such as a nitrile, chloride, iodide, and ester are readily tolerated. The conversion of an alkenyl iodide bearing a keto group to the corresponding silylated cyanohydrin allows preparation of the corresponding Grignard reagent affording, after acylation and deprotection, unsaturated 1,4-diketones.

Copper-catalyzed synthesis of vinyl sulfides

(Chemical Equation Presented) We report a method for the synthesis of vinyl sulfides using the soluble copper(I) catalyst [Cu(phen)(PPh3) 2]NO3. The desired vinyl sulfides are obtained in good to excellent yields, with retention of stereochemistry. This protocol tolerates a wide variety of functional groups or substrates, is palladium-free, and does not require the use of expensive or air-sensitive additives.

Electroinitiated Oxygenation of Alkenyl Sulfides and Alkynes in the Presence of Thiophenol

Electrolysis of alkenyl sulfides in the presence of thiophenol with bubbling of molecular oxygen gave the corresponding α-(phenylthio) carbonyl compounds with the consumption of a catalytic amount of electricity.An electroinitiated radical chain mechanism has been proposed.The reaction also took place without electrochemical initiation, but much (5-50 times) longer reaction time was required for the completion of the reaction.The potential utility of the present reaction in organic synthesis is demonstrated by the net 1,2-transposition of a phenylthio group and a carbonyl group.The electroinitiated oxygenation of ketene dithioacetals also proceeded smoothly to give the corresponding α-(phenylthio) thiol esters.It was also found that the electroinitiated oxygenation of alkynes in the presence of thiophenol gave α-(phenylthio) carbonyl compounds.A mechanism involving the initial formation of alkenyl sulfides has been proposed.

Facile Reduction of Dithiocarbonates Derived from Secondary Alcohols with n-Bu3SnH-Et3B and Synthesis of 2-Furanthiones and 2-Furanones by Intramolecular Addition of Alkoxythiocarbonyl Free Radicals to Acetylenic Linkages

The reduction of dithiocarbonates or thiocarbonates by n-Bu3SnH-Et3B easily gives the corresponding hydrocarbons.The intermediate alkoxythiocarbonyl radical equivalents are trapped by properly located carbon-carbon multiple bonds.The dithiocarbonates derived from either homopropargylic or homoallylic alcohols produce tetrahydrofuranones upon treatment with n-Bu3SnH-Et3B.Application of this new method to the conversion of carbonyl compounds into olefins is also described.

PALLADIUM-CATALYZED REACTIONS OF TRIALKYLSTANNYL PHENYL SULFIDES WITH ALKENYL BROMIDES. A NEW DIASTEREOSELECTIVE SYNTHESIS OF (E)-1-ALKENYL PHENYL SULFIDES

The reaction of easily available stereoisomeric mixtures of 1-alkenyl bromides with molar excesses of trialkylstannyl phenyl sulfides takes place readily in the presence of Pd(PPh3)4 to afford diastereoselectively (E)-1-alkenyl phenyl sulfides in excellent yields.

CLEAVAGE OF SILICON-VINYL CARBON BOND BY nBu4NF

Dimethylphenylsilyl- and diphenylmethylsilyl-vinyl carbon bonds are cleaved with nBu4NF.Desilylation of 1-phenylthio-1-trimethylsilyl-1-alkenes in the presence of aldehyde moiety gives carbanion adducts.