
%0 Journal Article
%A Badali, F 
%A Karalis, A 
%A Tham, WY 
%A White, JM 
%T Evidence for Silicon-Directed Acid-Catalysed Ring Opening of a &#946;,&#947;-Epoxy Silane: Reaction of 1,1-Dimethyl-1-silacyclohex-3-ene Oxide With p-Nitrobenzoic Acid
%J Australian Journal of Chemistry
%D 1996/12/01
%V 49
%N 12
%P 1293-1299
%K 
%R https://doi.org/10.1071/CH9961293
%U https://www.publish.csiro.au/paper/CH9961293 
%X The ring-opening reaction of the &#946;,&#947;-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 &#946;-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 &#963;C- Si -&#963;* 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. 
