62762-20-3

Usage

Physical properties

colorless liquid; bp 130–134 °C/15 mmHg

Preparation

1-Phenylthio-1-trimethylsilylethylene is widely used by lithiation of phenyl vinyl sulfide with lithium diisopropylamide, followed by silylation, or the base-induced elimination of 2-chloro-1-trimethylsilyl-1- phenylthioethane, or the lithiation of ethyl phenyl sulfoxide with LDA followed by silylation, or the Pd-catalyzed coupling reactions of trimethylstannyl phenyl sulfide with 1-bromo-1-trimethylsilylethylene.

Upstream product

• 17988-58-8 12-<(phenylthio)ethyl>trimethylsilane 
• 130083-71-5 (1-Methoxy-1-phenylsulfanyl-ethyl)-trimethyl-silane 
• 75-77-4 chloro-trimethyl-silane 
• 1822-73-7 phenylthioethylene 
• 37891-39-7 trimethylsilane 
• 17873-08-4 (phenylsulfanylmethyl)trimethylsilane 
• 100-68-5 methyl-phenyl-thioether 
• 754-05-2 ethenyltrimethylsilane 
• 931-59-9 benzenesulfenyl chloride 
• 108-98-5 thiophenol 
• 5535-49-9 2-Chloroethyl phenyl sulfide 
• 2973-86-6 lithium thiophenoxide 
• 1066-54-2 trimethylsilylacetylene 
• 72610-21-0 2-chloro-1-(trimethylsilyl)ethyl phenyl sulfide 

Downstream Products

• 107014-81-3 6-phenylthioundec-5-ene 
• 85969-82-0 2,2-dimethyl-4-phenylthio-4-trimethylsilyloctane 
• 76200-39-0 1-phenylthio-1-trimethylsilylhexane 
• 107014-78-8 3-phenylthio-oct-3-ene 
• 107014-84-6 (1-phenylthiohexylidene)cyclohexane 
• 107014-88-0 (1-phenylthio-2-phenylethylidene)cyclohexane 
• 82632-31-3 (E)-4-Phenylsulfanyl-4-trimethylsilanyl-but-3-en-2-one 
• 82632-32-4 (E)-1-Phenyl-3-phenylsulfanyl-3-trimethylsilanyl-propenone 
• 107014-80-2 3-phenylthio-oct-2-ene 
• 105494-76-6 1-phenyl-2-phenylthio-2-trimethylsilylhexane 
• 107014-87-9 2-phenylthio-1-phenylhept-2-ene 
• 76200-41-4 trimethyl(2-phenyl-1-(phenylthio)ethyl)silane 
• 105494-75-5 1-phenyl-2-phenylthio-2-trimethylsilylpropane 
• 107014-83-5 3-phenylthio-2-phenyloct-2-ene 

Relevant academic research and scientific papers

ALDEHYDES FROM ALKYLLITHIUMS WITH 2-CARBON HOMOLOGATION

1-Phenylthio-trimethylsilylalkanes, which are readily converted to aldehydes, are prepared by the addition of alkyllithiums to phenylthioethene, trimethylsilylethene and 1-phenylthio-1-trimethylsilylethene.

New method for the synthesis of indenes

A new two-step method was developed for the synthesis of 2-sulfonyl-substituted indenes from aromatic aldehydes. The reactions of 1-phenylsulfonyl-1-(trimethylsilyl)ethylene with ortho-lithiated derivatives of aromatic and heteroaromatic aldehydes afford conjugate addition products whose subsequent cyclization gives substituted 2-sulfonylindenes in preparative yields. The reactions of 2-(phenylsulfonyl)indenes with Grignard reagents were studied. It was shown that the sulfonyl group can be replaced in the presence of iron(III) acetylacetonate.

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

Metalation reactions. XXIV. Metalation of (vinylthio)benzene

The addition of organolithium compounds to (vinylthio)benzene (1) and then an electrophilic quenching followed by a further metalation/electrophilic quenching is a general method to prepare in one pot (alkylthio)benzenes ortho, alpha-substituted with equal or different groups. The direct dimetalation of 1 affords the ortho, alpha-dilithiated species 15 besides other by-products. Starting from 15 it is possible to obtain in one step ortho, alpha-substituted (vinylthio)benzenes and heterocyclic compounds.

Electro-initiated oxygenation of alkenylsilanes in the presence of thiophenol

Electrolysis of alkenylsilanes 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 electro-initiated radical chain mechanism i

A highly stereoselective synthesis of (z)-1-phenylthio-1-trialkyl- silylalkenes from 1-methoxy-1-phenylthio-1 - trialkylsilylalkanes

A new method for the highly stereoselective synthesis of (Z) -1-phenylthio-1-trialkylsilylalkenes 3 by the elimination of methanol from 1-methoxy-1-phenylthio-1-trialkylsilylalkane 2 in organic solvents is described.

A Facile Stereoselective Synthesis of α-Silyl Substituted Vinyl Sulfides

A facile one-pot synthesis of α-silyl substituted vinyl sulfides which involves the chlorination of 1-phenylthio-1-silylalkanes followed by dehydrochlorination is 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.

ELIMINATIVE DEOXYGENATION: THE FACILE FORMATION OF α-TRIMETHYLSILYL VINYL SULFIDES FROM SULFOXIDES

Synthetically useful α-trimethylsilyl vinyl sulfides are generated in high yields by deoxygenation of the corresponding sulfoxides in the presence of excess LDA and trimethylsilyl chloride.