Phenylsulfonylethyl trimethylsilane

Georges Hareau Philip Kocienski University of Southampton, Southampton, UK 

Solubility sol all common ethereal, halocarbon, and hydrocarbon solvents. 

Preparative Methods (2-phenylsulfonylethyl)trimethylsilane (2) is prepared by radical addition of thiophenol to vinyltrimethylsilane to give (2-phenylthioethyl)trimethyl-silane (1), which is then oxidized with hydrogen peroxide (eq 1).2 3 

General Considerations. A sequence involving metalation, alkylation, and fluoride-induced elimination of benzenesulflnate 

Alternative Routes to Substituted (2-Phenylsulfonylethyl)-trimethylsilanes. Although the fluoride-induced elimination is a reliable and efficient method for synthesizing alkenes, the requisite silyl sulfone precursors are often better prepared by methods which avoid the use of (2). For example, eq 3 illustrates an alternative synthesis of 2,2-dialkyl-2-(phenylsulfonylethyl)trimethyl-silanes involving alkylation of a lithio sulfone with (iodomethyl)-trimethylsilane.  

General Considerations. A sequence involving metalation, alkylation, and fluoride-induced elimination of benzenesulfinate allows the conversion of (2) to a terminal alkene. An analogous sequence involving a double alkylation of (2) provides a 1,1-disubstituted alkene (eq 2). The Uthio derivative of (2) has also been used to prepare cyclopropyUdene derivatives, homo-allylic alcohols, and aUyl silanes via the Julia alkenation.  

2-(Phenylsulfonylvinyl)trimethylsilane (3) is a useful acetylene equivalent for use in Diels-Alder reactions (eq 

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