The condensation of deoxybenzoin, phenylacetone, dibenzyl ketone and ethyl phenyl ketone with primary aromatic amines results in imines, which tautomerize partially in solution with measurable rate to the corresponding enamines. The condensation with methylamine produces instantly the isomer composition. In several cases the imines show syn-anti- isomerism. The structural dependence of the imine-enamine-equilibrium is discussed.
