75717-41-8

Upstream product

• 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 
• 52356-93-1 (Z)-1-octenyl iodide 
• 882-33-7 diphenyldisulfane 
• 629-05-0 n-octyne 
• 108-98-5 thiophenol 
• 87514-05-4 Trimethyl-((Z)-1-phenylsulfanyl-oct-1-enyl)-silane 
• 13910-16-2 n-octylsulfanylbenzene 
• 3561-67-9 bis(phenylthio)methane 
• 111-71-7 heptanal 

Downstream Products

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

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.

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.

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.