PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE Property

Melting point:

51-52 °C(lit.)

Boiling point:

347.4±34.0 °C(Predicted)

Density 

1.040±0.06 g/cm3(Predicted)

Flash point:

>230 °F

solubility 

sol all common ethereal, halocarbon, and hydrocarbon solvents.

form 

solid

CAS DataBase Reference

73476-18-3

Safety

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

29310099

Hazard and Precautionary Statements (GHS)

PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE Chemical Properties,Usage,Production

Chemical Properties

white fine crystalline powder

Physical properties

mp 52 °C.

Uses

(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.

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.]