Chloromethyltrimethylsilane, Grignard reagent from

The Grignard reagent prepared from chloromethyltrimethylsilane (30 mmol) and Mg (36 mg atom) in ether (20 ml) was added dropwise to diphenyl phosphorazidate (27 mmol) in ether (40 ml), keeping the temperature below 0°C. The reaction mixture was stirred for 2 hat 0 C, and then at ambient temperature for 3 h. It was then cooled to 0 °C, and ice-water was added. The mixture was filtered, and the solid was washed with ether. The combined ethereal extracts were washed with ice-water and dried. Careful concentration at <45 °C/atmospheric pressure, then distillation at... 

Trialkylsilyl groups have a modest stabilizing effect on adjacent carbanions (see Part A, Section 3.4.2). Reaction of the carbanions with carbonyl compounds gives (3-hydroxyalkylsilanes. (3-Hydroxyalkylsilanes are converted to alkenes by either acid or base.270 These eliminations provide the basis for a synthesis of alkenes. The reaction is sometimes called the Peterson reaction.211 For example, the Grignard reagent derived from chloromethyltrimethylsilane adds to an aldehyde or ketone and the intermediate can be converted to a terminal alkene by acid or base.272... 

For example, the Grignard reagent derived from chloromethyltrimethylsilane adds to an aldehyde or ketone and the intermediate can be converted to a terminal alkene by base. ... 

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