Reduction of aromatic imino derivatives: Chemical, electrochemical, and theoretical studies

The reduction of aromatic phenyl, naphthyl, and anthryl imino derivatives was studied by chemical, electrochemical, and theoretical methods. The behavior of the imines in the presence of reducing agents depended on the aryl group. When the imine group is sterically blocked, chemical reduction begins at the aromatic ring. Electrochemical reduction depends on the aromatic ring: Compounds containing phenyl or naphthyl groups are reduced at the imine bond, while those with an anthryl group are reduced at the aromatic ring. These results are explained by theoretical calculations which suggest that the different steps operate in the fast equilibrium.