Substituted cyclohexenylsilanes (2), (5), (9), and (13) undergo Friedel–Crafts reactions to give substitution products, site-selectively at the carbon atom carrying the trimethylsilyl group. β-Trimethylsilylstyrene (17) similarly gives more substitution in Friedel–Crafts reactions with benzoyl chloride and with phenylacetyl chloride than styrene itself. The syntheses of the silanes are reported, and some limitations of the idea identified.
I. Flaming and A. Pearce, J. Chem. Soc., Perkin Trans. 1, 1980, 2485 DOI: 10.1039/P19800002485
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