64489-07-2

Upstream product

• 18178-59-1 (E)-1,2-bis(trimethylsilyl)ethene 
• 98-09-9 benzenesulfonyl chloride 
• 32501-93-2 1-(Phenylsulfonyl)-2-(trimethylsilyl)acetylene 
• 873-55-2 sodium benzenesulfonate 
• 754-05-2 ethenyltrimethylsilane 
• 14630-40-1 Bis(trimethylsilyl)ethyne 

Downstream Products

• 82201-45-4 C₂₅H₂₆O₂SSi 
• 82262-89-3 ((1R,2S,3R,4S)-3-Benzenesulfonyl-bicyclo[2.2.1]hept-5-en-2-yl)-trimethyl-silane 
• 73476-18-3 1-benzenesulfonyl-2-trimethylsilylethane 
• 84363-58-6 4-(phenylsulfonyl)-5-(trimethylsilyl)-1-pentene 
• 97399-04-7 2-(phenylsulfonyl)-1,2-bis-(trimethylsilyl)ethane 
• 82263-29-4 C₃₆H₃₆O₃SSi 
• 82201-49-8 C₃₀H₃₄O₂SSi 
• 82201-47-6 C₂₅H₂₅⁽²⁾HO₂SSi 
• 82201-48-7 C₂₆H₂₈O₂SSi 

Relevant academic research and scientific papers

Simple and efficient synthesis of the acetylene equivalent (E)-1-benzenesulfonyl-2-(trimethylsilyl)ethylene

The acetylene equivalent (E)-1-benzenesulfonyl-2-(trimethylsilyl)ethylene is readily synthesized in a one-pot reaction, in excellent yield under very mild reaction conditions, via iodosulfonylation-dehydroiodination of vinyltrimethylsilane.

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.

Dienophilic Properties of Phenyl Vinyl Sulfone and trans-1-(Phenylsulfonyl)-2-(trimethylsilyl)ethylene. Their Utilization as Synthons for Ethylene, 1-Alkenes, Acetylene, and Monosubstituted Alkynes in the Construction of Functionalized Six-Membered Rings via ? Cycloaddition Meth.

Useful procedures for effecting the indirect capture of ethylene, acetylene, 1-alkenes, and monosubstituted alkynes in Diels-Alder cycloadditions have been developed.In the first sequence, phenyl vinyl sulfone is shown to enter into ? reactions as a moderately reactive dienophile and to do so with very good regioselectivity.The resulting adducts can be directly desulfonated or alkylated prior to such reduction.A wide range of functional groups can be appended in this fashion at a specific locus within the newly formed six-membered ring.When the analogous chemistry is applied to trans-1-(phenylsulfonyl)-2-(trimethylsilyl)ethylene (2), adducts result which undergo ready fluoride ion induced elimination with efficient introduction of a double bond.The use of 2 and its d2 derivative is highlighted by the synthesis of several functionalized dibenzobarrelenes.

SILICON IN ORGANIC SYNTHESIS. 12. trans-1-BENZENESULFONYL-2-(TRIMETHYLSILYL)ETHYLENE, A DIELS-ALDER DIENOPHILE EQUIVALENT OF ACETYLENE AND MONOSUBSTITUTED ACETYLENES

trans-1-Benzenesulfonyl-2-(trimethylsilyl)ethylene and its 1,2-d2 derivative enter into Diels-Alder cycloaddition to give products which are smoothly eliminated with fluoride ion.Alkylation of the α-sulfonyl carbanion can precede elimination, s