The fact that oxidative dealkylation occurs with i Pr 2 NH 31 and not with Et 2 NH 28 suggests that amidation as well as hemiaminal decomposition to RNH 2 is driven by steric factors that influence the ratio of rates of amidation and oxidative dealkylation: Et 2 NH 28 is a significantly better nucleophile than i Pr 2 NH 31 and therefore amidation is expected to be faster. In contrast, α-C-H oxidation is more rapid for i Pr 2 NH 31, but nucleophilic attack of cyanide at the sterically bulkyl hemiaminal or iminium intermediate is disfavored, while hydrolysis to acetone and i PrNH 2 is favored due to release of steric strain.