73476-18-3C[Si](C)(C)CCS(=O)(=O)c1ccccc1IVPQHMQOYMNETK-UHFFFAOYSA-N73476-18-3DTXSID20369308white fine crystalline powder
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용도(2-Phenylsulfonylethyl)trimethylsilane is widely used as reagent for the synthesis of mono- and 1,1-disubstituted alkenes via sulfone metalation, alkylation, and fluoride-induced elimination.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 lithio derivative of (2) has also been used to prepare cyclopropylidene derivatives, homoallylic alcohols, and allyl silanes via the Julia alkenation.
(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).
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