The Hydrolysis of β-Acetal Cobaloximes
Silverman, R.B. and David Dolphin
J. Organomet. Chem.
Cobaloxime (I) remained unchanged after five days at room temperature in CH2Cl2 containing Et3NH+Br-/Et3N. Under the same conditions, II decomposed to give a mixture of the starting material II (27%), III (18%), and unalkylated cobaloxime (55%). The stability of the cyclic acetal I relative to II under mildly protic conditions was rationalized by the proximity of the eliminated alcohol to the incipient carbonium ion center.