The mechanism of hydrolysis of 2,3-OO-benzylidene-norbornane-exo-2,-exo-3-diols
Abstract
The hydrolyses of the isomeric 2,3-OO-benzylidene-norbornane-exo-2,exo-3-diols occur at similar rates to their interconversion: interconversion of the corresponding p-methoxybenzylidene compounds is much faster than their hydrolysis and interconversion of the p-nitrobenzylidene compounds is slower than their hydrolysis; the hydrolyses may proceed through a bimolecular attack of water on the conjugate acid.