2,6-Dinitro-4-X-anilino-N-methylpropionamides: reactions with potassium methoxide

Abstract

The interactions between potassium methoxide and compounds of the type 2,6-dinitro-4-substituted anilinopropionamides (I) have been studied kinetically over a range of temperatures in methanol. The formation of a Meisenheimer complex is shown to occur with σ-bond formation at the 1-position of the aniline and the reasons for the observation of this path rather than anilino N–H ionization or 3-σ complex formation are discussed.