| Identification | Back Directory | [Name]
PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE | [CAS]
73476-18-3 | [Synonyms]
PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE
(2-Phenylsulfonylethyl)trimethylsilane
1-(phenylsulfonyl)-2-(trimethylsilyl)ethane
PHENYL 2-(TRIMETHYLSILYL)ETHYL SULFONE, 99+%
1-(Phenylsulfonyl)-2-(trimethylsilyl)ethane, 2-(Phenylsulfonyl)ethyltrimethylsilane, 2-(Trimethylsilyl)ethyl phenyl sulfone | [Molecular Formula]
C11H18O2SSi | [MDL Number]
MFCD00015929 | [MOL File]
73476-18-3.mol | [Molecular Weight]
242.41 |
| Chemical Properties | Back Directory | [Appearance]
white fine crystalline powder | [Melting point ]
51-52 °C(lit.)
| [Fp ]
>230 °F
| [solubility ]
sol all common ethereal, halocarbon, and hydrocarbon
solvents. | [form ]
solid | [CAS DataBase Reference]
73476-18-3 |
| Hazard Information | Back Directory | [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.] |
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