
TY  - JOUR
A1  - Badali, F 
A1  - Karalis, A 
A1  - Tham, WY 
A1  - White, JM 
T1  - 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
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1996
VL  - 49
IS  - 12
SP  - 1293
EP  - 1299
KW  - 
UR  - https://doi.org/10.1071/CH9961293 
N2  - 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. 
ER  -

