Journal of Chemical Research

The electrophilic substitution of some 2, 4-and 2, 6-dihaloacetanilides

JR Hanson, H Saberi

Index: Hanson, James R.; Saberi, Hamid Journal of Chemical Research, 2004 , # 10 p. 699 - 701

Full Text: HTML

Citation Number: 0

Abstract

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 ...