In principle, the alkene could react with the electrophile at either end but reaction next to silicon leads to the more stable cation β to silicon. In the vinyl silane, the C-Si bond is orthogonal to the p orbital of the π bond, but as the electrophile attacks, the silyl group starts to move upwards, increasing the interaction between the C-Si bond and the empty p orbital of the cation. Rotation is restricted and the C-Si bond stabilization is decreased, resulting in the quick removal of the silyl group to form the alkene which retains it’s geometry.
I. Fleming, A. Barbero and D. Walter, Chem. Rev., 1997, 97, 2063–2192.
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