Vol. 79 perchlorate ion is not nucleophilic, this imine probably reacts almost entirely by SnI in dilute perchloric acid. 1,2-Iminoethane probably reacts only by Sn2. The other imines would react by a combination of SnI and Sn2. The relative rates of these acid-catalyzed hydrations of imines can be accounted for on the basis of a transition from SnI to Sn2 mechanism as in the case of epoxides24 and the assumption that reaction is predominantly Sn2 at a primary carbon atom, a mixture of SnI and Sn2 at a secondary carbon atom and predominantly SnI at a tertiary carbon atom.
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