22103-05-5

Usage

InChI:InChI=1/C9H10S/c1-2-8-10-9-6-4-3-5-7-9/h2-8H,1H3

Upstream product

• 5296-64-0 allyl phenyl thioether 
• 161573-73-5 <(etoxycarbonyl)(phenylsulfinyl)methylene>triphenylphosphorane 
• 590-15-8 trans-2-propenyl bromide 
• 108-98-5 thiophenol 
• 590-14-7 1-bromo-1-propene 
• 930-69-8 sodium thiophenolate 
• 70030-50-1 but-2-enethioic acid S-phenyl ester 
• 497-23-4 2-buten-4-olide 
• 702-04-5 crotyl phenyl sulfide 
• 15486-58-5 1,1-bis(phenylthio)propane 
• 6212-77-7 1-phenylthio-1-propyne 
• 590-13-6 (Z)-1-propenyl bromide 
• 106-95-6 allyl bromide 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 28691-72-7 (E)-1-propenyl phenyl sulfone 
• 229332-55-2 (E)-3-methyl-2-(phenylsulfonyl)-2-propenyl alcohol 
• 77199-25-8 trans-α-Methyl-β-phenylthioacrylic acid 
• 36219-91-7 1-phenylthio-2-phenylprop-1-ene 
• 55064-96-5 2-(phenylthio)propanal 
• 27064-03-5 S-phenyl methanethioate 
• 132585-92-3 (4S,4aS,6R,7R,7aR)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2,7-trimethyl-6-phenylsulfanyl-tetrahydro-furo[3,2-d][1,3]dioxine 
• 118629-83-7 1(R*)-(dimethoxymethyl)-2(S*)-(phenylthio)-3(S*)-methyl-4(S*)-<(2,4-dinitrophenyl)amino>-8-methoxy-1,2,3,4-tetrahydronaphthalene 
• 103853-13-0 1-Phenylmercapto-2-aethylmercapto-propan 

Relevant academic research and scientific papers

Multifaceted strategy for the synthesis of diverse 2,2′-bithiophene derivatives

New catalytically or high pressure activated reactions and routes, including coupling, double bond migration in allylic systems, and various types of cycloaddition and dihydroamination have been used for the synthesis of novel bithiophene derivatives. Tha

Radical Cation Cycloadditions Using Cleavable Redox Auxiliaries

The incorporation of an easily oxidized arylsulfide moiety facilitates the photocatalytic generation of alkene radical cations that undergo a variety of cycloaddition reactions with electron-rich reaction partners. The sulfide moiety can subsequently be reductively cleaved in a traceless fashion, affording products that are not otherwise directly accessible using photoredox catalysis. This approach constitutes a novel oxidative “redox auxiliary” strategy that offers a practical means to circumvent a fundamental thermodynamic limitation facing photoredox reactions.

Nickel-catalyzed electrochemical synthesis of dihydro-berazo[b]thiophene derivatives

The intramolecular electrochemical reductive cyclization of orthohaloaryl allyl thioethers catalyzed by Ni(II) complexes associated to cyclam ligands affords dihydro-benzo[b]thiophene derivatives in moderate to good yields.

Double bond migration in S-allyl systems catalysed by [RuC1H(CO)(PPh3)3]

Reactions of S-allyl systems (allyl sulphides of R-S-allyl type, where R = Et, allyl, Ph, Me3C, Ph3C, as well as of allyl phenyl sulphoxide, allyl phenyl sulphone, 2,5-dihydro-1,1-dioxothiophene) with [RuClH(CO) (PPh3)sub

Regio- and stereospecific cleavage of stannylepoxides with lithium phenylsulfide

Unsubstituted and α or β C-substituted epoxystannanes react with lithium phenylsulfide to give regio- and stereodefined α-phenylthio-β-hydroxystannanes resulting from α-opening with inversion of configuration. On the other hand, α- or β-trans-silyl epoxys

Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 15. Generation of alkoxycarbonyl(sulfenyl)carbenes and their intramolecular insertion to give alkenyl sulfides

A range of 18 alkoxycarbonyl sulfinyl phosphorus ylides 9 have been prepared and their behaviour upon flash vacuum pyrolysis (FVP) at 600 deg C examined. For R1 = H, Me and Et they lose Ph3PO and in some cases Ph3P to give mixtures of products including the alkenyl sulfides 10, the sulfides 11, the disulfides 12 and the thioesters 14. The alkenyl sulfides 10 most likely arise from intramolecular insertion of the alkoxycarbonyl sulfenyl carbenes resulting from loss off Ph3PO to produce β-lactones which then lose CO2 and this is supported by the results from 13C labelled ylides. Possible mechanisms for the formation of 11 and 14 are also presented and the feasibility of various steps has been examined by preparation and pyrolysis of the proposed intermediates. In contrast, pyrolysis of the ylides 9 where R1 = Ph and the tert-butoxycarbonyl ylides 30 leads mainly to complete fragmentation with loss of Ph3PO and benzyl alcohol or 2-methylpropan-2-ol and does not give any useful sulfur-containing products. Four alkoxy-carbonyl sulfonyl diazo compounds 33 have been prepared and in three cases they give the alkenyl sulfones 34 upon FVP at 400 deg C, probably by an intramolecular insertion and decarboxylation process analogous to the formation of 10 from 9. On the other hand the alkoxycarbonyl carbenes produced by FVP of the amino acid-derived diazo compounds 35 undergo alternative proocesses with no sign of β-lactone formation. Fully assigned 13C NMR data are presented for 13 of the ylides.

First synthesis, X-ray structure analysis and reactions of alkenyltriphenylbismuthonium salts

Treatment of triphenylbismuth difluoride with alkenyltrimethylsilanes 1 or trimethylsilyl cyanidealkenyltrialkylstannanes 3 in the presence of boron trifluoride-diethyl ether gave the corresponding alkenyltriphenylbismuthonium tetrafluoroborates 2 in moderate to good yields. An X-ray crystallographic analysis of the salt 2e confirmed the distorted tetrahedral geometry of the central bismuth atom. When treated with a sulfinate 5 or the thiolate 11, the salts 2 readily transferred both the vinyl and phenyl moieties to these nucleophiles to afford the sulfones 7-10 or the sulfides 12, 13, respectively. In the presence of a palladium catalyst, the salt 2e underwent the Heck-type reaction with ethyl acrylate 17 to afford the dienoate 18 and cinnamate 19 in moderate yields. Action of KOBut on the salt 2b yielded p-tolylacetylene 22, while a similar reaction with the salt 2e in the presence of the styrenes 23 gave the cyclopropanes 24. A Hammett study of the latter reaction has suggested a possible involvement of an alkylidenecarbene as the intermediate in these base-promoted reactions.

Low pressure hydrogenation of unsaturated sulphides with homogeneous and heterogeneous ruthenium catalysts

Ru2O·nH2O and [Ru3O(AcO)6(H2O)3]+AcO- were examined for catalytic activity in the hydrogenation of a series of unsaturated sulphides under heterogeneous and homogeneous conditions, respectively. By the appropriate combination of these two methodologies, a number of saturated sulphides could be synthesized in satisfactory to good yields, thus minimizing side reactions.

Isomerization processes in the synthesis of asymmetric allyl chalcogenides

Allyl-propenyl rearrangement (prototropic isomerization) occurs in the synthesis of allyl organyl chalcogenides in a hydrazine hydrate - KOH system with a 6 - 10-fold molar excess of KOH. Specificities of the rearrangement that depend on the nature of the chalcogen were studied.

Flash Vacuum Pyrolysis of Alkoxycarbonyl/Sulfinyl Stabilised Phosphorus Ylides: Generation and Intramolecular Insertion of Alkoxycarbonyl(sulfenyl)carbenes

Flash vacuum pyrolysis of phosphorus ylides stabilised both by ester and sulfinyl groups results mainly in extrusion of Ph3PO to generate alkoxycarbonyl(sulfenyl)carbenes; these undergo intramolecular insertion into CH of the alkoxycarbonyl group giving β-lactones which under the conditions lose CO2 to afford alkenyl sulfides.