EFFECT OF RING SIZE ON THE ACID-CATALYSED HYDROLYSIS OF CYCLIC α,β-EPOXYSILANES

Article abstract of DOI:10.1016/0022-328X(85)87059-5

Acid-catalysed hydrolysis of epoxysilanes derived from common-, medium- and large-ring vinylsilanes is described.Whereas the large epoxysilanes give ketones, the medium-ring epoxysilanes give transannular products and the common-ring epoxysilanes provide α,β-dihydroxysilanes.The results are explained as due to the conformational rigidity in the common-ring silyldiols and the conformational freedom in the large-ring silyldiols to achive antiperiplanar geometry for 1,2-elimination of trimethylsilanol.