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Useful ethylene equivalent in its reaction with electrophiles. The reactivity is controlled by the ability of the Si atom to stabilize a positive charge on a ß-carbon atom. See Appendix 4./n
Acylation under Friedel-Crafts conditions leads to vinyl ketones. Using ɑß-unsaturated acyl halides, the products are divinyl ketones, which, under the reaction conditions, undergo the Nazarov cyclization to enones: J. Org. Chem., 45, 1046 (1980):/n
For reviews of the Nazarov cyclization, see: Synthesis, 429 (1983); Org. React., 45, 159 (1994)./n
Coupling with the electrophilic reagent generated from an aryl iodide in the presence of Pd(OAc)2, triphenylphosphine and base, provides a route to styrenes: Chem. Lett., 1993 (1982)./n
Also undergoes regioselective addition reactions with alkyllithiums: J. Chem. Soc., Perkin 1, 1131 (1983), and Grignards: Chem. Ber., 117, 383 (1984), to giveɑ-metallated products./n
For use in a 2-carbon extension of aldehydes to ɑß-unsaturated aldehydes based on cycloaddition to the nitrone, see N-Methylhydroxylamine hydrochloride, L02202./n
For an extensive review of the reactions of vinyl (and allyl) silanes, see: Org. React., 37, 57 (1989)./n
Hazard Statements: H225-H315-H319-H335
Highly flammable liquid and vapour. Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P210-P280g-P243-P305+P351+P338-P403+P233
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves. Take precautionary measures against static discharge. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store in a well-ventilated place. Keep container tightly closed.