73476-18-3

Usage

Uses

Used in Chemical Synthesis:
PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE is used as a reagent for the synthesis of monoand 1,1-disubstituted alkenes via sulfone metalation, alkylation, and fluoride-induced elimination. PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE plays a crucial role in the conversion of specific precursors to terminal alkenes and 1,1-disubstituted alkenes through a series of chemical reactions, including metalation, alkylation, and fluoride-induced elimination.
Used in Organic Chemistry:
In the field of organic chemistry, PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE is used as a key intermediate in the preparation of various complex organic molecules. The lithio derivative of PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE has been employed to synthesize cyclopropylidene derivatives, homoallylic alcohols, and allyl silanes via the Julia alkenation, which are important building blocks in the synthesis of a wide range of organic compounds.
Used in Pharmaceutical Industry:
PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE may also find applications in the pharmaceutical industry, where it can be used as a starting material or intermediate for the synthesis of various drug candidates. Its unique chemical properties and reactivity make it a valuable tool in the development of new medications and therapeutic agents.
Used in Material Science:
In material science, PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE could potentially be utilized in the development of novel materials with specific properties, such as improved stability, reactivity, or selectivity. Its unique structure and chemical properties may contribute to the creation of advanced materials for various applications, including electronics, coatings, and adhesives.

Preparation

(2-phenylsulfonylethyl)trimethylsilane (2) is prepared by radical addition of thiophenol to vinyltrimethylsilane to give (2-phenylthioethyl)trimethylsilane (1), which is then oxidized with hydrogen peroxide).

Purification Methods

Dissolve it in Et2O, wash it with saturated HCO 3 followed by saturated NaCl, H2O and dried (MgSO4). Evaporation leaves residual crystals with m 52o. [Hsiao & Shechter Tetrahedron Lett 23 1963 1982, Bortolini et al. J Org Chem 53 2688 1985.]

InChI:InChI=1/C11H18O2SSi/c1-15(2,3)10-9-14(12,13)11-7-5-4-6-8-11/h4-8H,9-10H2,1-3H3

Upstream product

• 17988-59-9 phenyl 2-(trimethylsilyl)ethyl sulfide 
• 64489-07-2 cis-1-(phenylsulfonyl)-2-(trimethylsilyl)ethylene 
• 64489-06-1 trans-1-(benzylsulfonyl)-2-(trimethylsilyl)ethylene 
• 3112-85-4 methylphenylsulfonate 
• 2344-80-1 Chloromethyltrimethylsilane 
• 754-05-2 ethenyltrimethylsilane 
• 14630-40-1 Bis(trimethylsilyl)ethyne 
• 108-98-5 thiophenol 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 5535-48-8 PVS 
• 98-09-9 benzenesulfonyl chloride 
• 32501-93-2 1-(Phenylsulfonyl)-2-(trimethylsilyl)acetylene 
• 64489-03-8 1-benzenesulfonyl-2-chloro-2-trimethylsilylethane 

Downstream Products

• 80735-94-0 1-Phenyl-3-buten-1-ol 
• 84363-55-3 2-(phenylsulfonyl)-1-(trimethylsilyl)hexane 
• 84363-54-2 2-(phenylsulfonyl)-1-(trimethylsilyl)butane 
• 139242-76-5 (2S)-1-(Phenylmethoxy)-4-(phenylsulfonyl)-5-(trimethylsilyl)-2-pentanol 
• 144604-85-3 (2S,4RS)-2-hydroxy-4-phenylsulfonyl-5-trimethylsilyl-1-pentyl p-toluenesulfonate 
• 144604-85-3 Toluene-4-sulfonic acid (R)-4-benzenesulfonyl-2-hydroxy-5-trimethylsilanyl-pentyl ester 
• 112897-09-3 (3R)-1-(tert-butyldiphenylsilyloxy)hex-5-en-3-ol 
• 133827-10-8 (3R)-1-O-(t-butyldiphenylsilyl)-3-O-(trimethylsilyl)-1,3-dihydroxyhex-5-ene 
• 133218-77-6 (S)-5-Benzenesulfonyl-1-(tert-butyl-diphenyl-silanyloxy)-6-trimethylsilanyl-hexan-3-ol 
• 133218-82-3 (3S,5R)-1-O-tert-butyldiphenylsilyl-5-benzenesulfonyl-6-(trimethylsilyl)hexane-1,3-diol 
• 133218-77-6 (3S,5S)-1-O-tert-butyldiphenylsilyl-5-benzenesulfonyl-6-(trimethylsilyl)hexane-1,3-diol 
• 139242-75-4 (2S)-1-(tert-Butyldimethylsiloxy)-4-(phenylsulfonyl)-5-(trimethylsilyl)-2-pentanol 
• 1012886-24-6 (1-Benzenesulfonyl-2-octyl-cyclopropylmethyl)-trimethyl-silane 
• 29108-24-5 2-vinylcyclohexan-1-ol 

Relevant academic research and scientific papers

A general approach to iridoids by applying a new Julia olefination and a tandem anion-radical-carbocation crossover reaction

A unified, asymmetric approach to the total synthesis of naturally occurring iridoids is presented. The synthesis features a recently discovered ortho → α transmetalation of alkyl aryl sulfone carbanions, thus enabling Julia reactions, by which so far har

Activation of Si-Si bonds for copper(I)-catalyzed conjugate silylation

Several alkyl- and vinylsilanes were prepared through the copper(I)-catalyzed conjugate silylation of α,β-unsaturated compounds. Optimal reaction conditions were first investigated to realize the conjugate addition of a nucleophilic silicon species to poo

β,β-disilylated sulfones as versatile building blocks in organic chemistry - A new sulfonyl carbanion transmetalation

1,3-Bis(trimethylsilyl)propyl phenyl sulfone undergoes, in contrast to all reported sulfones bearing α-hydrogen atoms, an initial ortho metalation to an aryllithium at low temperature, which transmetalates quantitatively to the corresponding α-sulfonyl or

Bu2SnIH-promoted proximal bond cleavage of methylenecyclopropanes and successive radical cyclization and/or Pd-catalyzed coupling reaction

The unprecedented regioselective hydrostannation of methylenecyclopropanes to give vinyltins was achieved using dibutyliodotin hydride (Bu2SnIH), which could be applied to intramolecular radical cyclization. Copyright

A new silicon-mediated elimination-rearrangement

Treatment of trimethylsilylethanes bearing α-phenyl groups and β-phenylthio, phenylsulfonyl or cyano groups with LDA causes elimination-rearrangement mediated by the β-carbanionic species. Mechanistic conclusions are based on isotopic labelling experiment

Sulfone reagents in organic synthesis. VI. Sulfonyl- and silyl-substituted hydrocarbons as versatile carbanion precursors in organic synthesis

The basic organometallic chemistry of β-silyl-substituted acetylenic, vinylic and alkyl sulfones has been investigated, with attention being given to metallation, carbometallation and the chemical reduction of carbon-carbon unsaturation. 2-Trimethylsilylvinyl and 2-trimethylsilylalkyl sulfones underwent smooth and stereoselective lithiation with RLi on the carbon α to the sulfonyl group. Carbometallation of vinyl sulfones could be achieved with RMgX or LiCuR2, but acetylenic sulfones carbometallated smoothly only with LiCuR2; with RMgX or RLi, these acetylenes underwent alkyldesulfonylation. The utility in synthesis of these metallo derivatives of sulfonyl-silyl-hydrocarbons is discussed and their value in elaborating carbon skeletons is illustrated for the preparation of alkenes, allenes, carbocycles and stereo-defined vinyl sulfones.

PRACTICAL SYNTHESES OF ALLYLSILANES FROM 1-BENZENESULFONYL-2-TRIMETHYLSILYLETHANE

The methanesulfonates of the adducts of aldehydes and ketones with 1-(1-benzenesulfonyl-2-trimethylsilyl)ethyllithium are converted by sodium-amalgam to allylsilanes.