148230-18-6Relevant articles and documents
Vinyl ether hydrolysis XXVIII. The mechanism of reaction of methyl α-(2,6-dimethoxyphenyl)vinyl ether
Jones, J.,Kresge, A. J.
, p. 38 - 41 (2007/10/02)
The acid-catalyzed hydrolysis of methyl α-(2,6-dimethoxyphenyl)vinyl ether in aqueous solution at 25 deg C occurs with the hydronium ion catalytic coefficient kH+ = 2.86 M-1 s-1 and gives the solvent isotope effect kH+/kD+ = 3.68; this indicates that reaction occurs by rate-determining proton transfer from the catalyst to the substrate to generate an alkoxycarbocation intermediate.An oxygen-18 tracer study shows further that, despite the steric hindrance provided by its two ortho substituents, this cation then reacts by addition of water to the cationic carbon atom to generate a hemiacetal, and not by nucleophilic attack of water on the methyl group remote from the carbocationic center:
