{ALF} For an extensive review of the reactions of vinyl (and allyl) silanes, see: Org. React., 37, 57 (1989).

{uni_hamburg} Short: III/35C4

{ALF} 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.

{ALF} For use in a 2-carbon extension of aldehydes to ɑß-unsaturated aldehydes based on cycloaddition to the nitrone, see N-Methyl­hydroxyl­amine hydrochloride, L02202.

{ALF} For reviews of the Nazarov cyclization, see: Synthesis, 429 (1983); Org. React., 45, 159 (1994).

{ALF} 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).

{uni_hamburg} Short: II/2

{ALF} 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):

{ALF} 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.

{uni_hamburg} Short: III/35F

{ALD} Beilstein:4(4)3922