Abstract
The ring-opening reaction of the β,γ-epoxy silane (4) with p-nitrobenzoic acid in chloroform occurs regiospecifically to give the two hydroxy esters (14) and (15). The mechanism involves regiospecific ring opening giving the β-silicon-stabilized carbenium ion (18) which is captured by the p-nitrobenzoate counter ion. The solution conformation of (14) provides evidence for the presence of σC- Si -σ* C-O interactions between the ring C- Si bonding orbital and the C-OCOC6H4NO2 antibonding orbital. In acetone, reaction of (4) with p-nitrobenzoic acid takes a different pathway and results in acyclic products from solvent attack at the silicon.
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