Many of the differences in the properties of 2,6-disubstituted anilines when compared to the unsubstituted compounds, have been ascribed to the steric inhibition of resonance.1 In the case of 2,6-dimethylacetanilide this is reflected in the orientation of the substitution reactions of the aromatic ring.2 A chlorine atom is a comparable size to a methyl group. In a study of the deacetylation of 4-nitroacetanilides by sodium methoxide, Wepster found3 that the reaction of 4-nitro-2,5-dichloroacetanilide ...
