Reactions of Anils with Active Methyl Group. (2)

Abstract

In the condensation of quinaldine methiodide and anils, the difference in the speed of dye formation by various substituents in aniline nucleus of anils was measured by colorimetry and following results were obtained. The reaction speed increases by the order of m-nitro>> o-carboxyl>H>p-methyl>p-hydroxyl radicals on aniline nucleus of piperonylidene-aniline but the order is p-nitro>> m-nitro->p-bromo->H>p-methyl>p-methoxyl in the case of p-dimethyl-aminobenzilidene-aniline. This fact seems to point that according to the polarization effect of these radicals on -CH=N- bond, they are proportionate to the speed of hydrolysis and so that radicals having strong polarity such as -NO₂ promote the reaction whereas -OCH₃ -OH which have inverse effect, tend to decrease the speed of reaction.