7715-02-8

Upstream product

• 26785-74-0 2-benzyl-[1,3]-dithiolane 
• 74-88-4 methyl iodide 
• 108555-48-2 2-benzyl-4,4,5,5-tetradeuterio-1,3-dithiolane 
• 100-52-7 benzaldehyde 
• 67-68-5 dimethyl sulfoxide 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 536-74-3 phenylacetylene 
• 1779-54-0 methylthiomethyl(triphenyl)phosphonium chloride 
• 15362-00-2 phenylacetaldehyde dimethyl dithioacetal 
• 35453-05-5 methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane 

Downstream Products

• 6111-82-6 (E)-1-phenyl-1-hexene 
• 174814-21-2 3-methylthio-2-phenylacrolein-d1 
• 174814-20-1 3-methylthio-2-phenylacrolein 
• 125572-33-0 1-methyl-6-phenyl-1H-imidazo[4,5-b]pyridine 
• 830321-02-3 (E)-1-(cyclohexylthio)-2-phenylethene 
• 621-82-9 Cinnamic acid 

Relevant academic research and scientific papers

Nickel-Catalyzed Inter- and Intramolecular Aryl Thioether Metathesis by Reversible Arylation

A nickel-catalyzed aryl thioether metathesis has been developed to access high-value thioethers. 1,2-Bis(dicyclohexylphosphino)ethane (dcype) is essential to promote this highly functional-group-tolerant reaction. Furthermore, synthetically challenging macrocycles could be obtained in good yield in an unusual example of ring-closing metathesis that does not involve alkene bonds. In-depth organometallic studies support a reversible Ni0/NiII pathway to product formation. Overall, this work not only provides a more sustainable alternative to previous catalytic systems based on Pd, but also presents new applications and mechanistic information that are highly relevant to the further development and application of unusual single-bond metathesis reactions.

The reactions of DMSO with arylaldehydes in the presence of sodium hydride

Dimethyl sulfoxide (DMSO) reacted with arylaldehydes under basic conditions to afford sulfide 1, β-(benzyloxy)styrene 2 and dialkyl sulfoxide 3, while the reaction of benzophenone with DMSO gave 1,1-diphenylethylene 4, 1,1-diphenyl-2-methylthioethylene 5 and sulfoxide 6 at the same time under the same conditions.

Studies of triphenylsilanethiol addition to alkynes: Preparation of vinyl sulfides

The scope and limitations of triphenylsilanethiol (1) a solid hydrogen sulfide equivalent, were investigated in free radical reactions to terminal alkynes. The triphenylsilylthioenol ether intermediate thus obtained was deprotected with Cs2CO3 in the presence of various electrophiles to yield mixtures of E and Z vinyl sulfides. The ratio of E and Z isomers could be controlled by varying the concentration of the starting alkynes.

A simplified preparation of vinyl sulfides, selenides and tellurides by a Wittig-type reaction

The preparation of several vinyl sulfides, selenides and tellurides by Wittig-type reaction in a one-pot procedure is described. The chalcogenyl triphenylphosphoranes 3 are formed 'in situ' by the reaction of chloromethyl phenyl chalcogenide, potassium tert-butoxide and triphenylphosphine. Reaction of 3 with carbonyl compounds affords the vinyl chalcogenides 6-9 with preferential Z-configuration.

A new generation of 'instant ylids': Powder mixtures of phosphonium salts and potassium hydride as storable precursors to Wittig reagents

Mixing a finely pulverized alkyltriphenylphosphonium salt and potassium hydride in 1:1 molar ratio gives a ready-to-use powder the components of which react rapidly when tert-butyl methyl ether is added under stirring. When, in general after a few minutes, the generation of the (triphenylphosphonio)alkanide is complete, it can be immediately used for the Wittig olefination of a carbonyl compound. Compared to sodium amide based 'instant ylids', the new blends offer little advantage as long as simple phosphonium salts are ingredients but they extend considerably the shelf life of mixtures containing heterosubstituted derivatives such as methylthiomethyl- or picolyltriphenylphosphonium salts. Copyright (C) 1996 Elsevier Science Ltd.

Ring Fragmentations of 2-Alkenyl- and 2-Benzyl-1,3-dithiolanes Induced by Bases. A Novel Method for the Preparation of 1,1-Bisalkylthio- or 1-Alkylthio-alk-1-enes and -alka-1,3-dienes

The reaction of 2-alkenyl- and 2-benzyl-1,3-dithiolanes with several bases and successive alkylation with alkyl halides has been investigated.In the reaction of 2-alk-1-enyl-1,3-dithiolanes with organolithium reagents and alkyl halides, deprotonation at C

The Formation of Vinyl Sulfides by the Cleavage of the Carbon-Sulfur Bond in Dithioacetals with CuCl2

The elimination of arene- and alkanethiol from diaryl and dialkyl dithioacetals, in the presence of copper(I) or copper(II) salt plus tertiary amine, to produce the corresponding aryl and alkyl vinyl sulfides, respectively, has been studied.The employment of a combination of 2 mol equiv. of CuCl2 and 2 mol equiv. of N,N-diisopropylethylamine is most favorable.

Stereospecific Reductive Desulfinylation of 1-Aryl-2-(methylsulfinyl)-2-(methylthio)ethenes with Grignard Reagents

(E)-1-Aryl-2-(methylsulfinyl)-2-(methylthio)ethene, obtained by the Knoevenagel-type condensation of methyl (methylthio)methyl sulfoxide with the corresponding aromatic aldehyde, was found to react with ethylmagnesium chloride to give (Z)-1-aryl-2-(methylthio)ethene predominantly.Since the reaction of (Z)-1-(methylsulfinyl)-1-(methylthio)-2-phenylethene afforded (E)-1-(methylthio)-2-phenylethene, the present reaction appeared to be stereospecific.