I understand that imines can be hydrolyzed in acidic medium. But what about in basic medium? Can imines still be hydrolyzed?

I have a plausible mechanism ... nitrogen's withdrawal of electron density makes the alpha proton relatively acidic; base abstracts the proton in an E2 reaction; nitrogen then takes back a proton to regenerate the base catalyst.

Is this correct? Does this actually happen?

  • $\begingroup$ In analogy to a carbonyl, why not attack directly at the imine's electrophilic carbon with your basic nucleophile to create a tetrahedral intermediate? Your proposed removal of an alpha-proton does occur in the enamine formation process. $\endgroup$ – ron Oct 28 '14 at 20:28

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