Kinetics of the reactions of nitro-substituted N-alkylacetanilides with sodium methoxide in methanol

Abstract

The sodium methoxide-catalysed methanolysis of N-ethyl-(3) or N-methyl-2′,4′,6′-trinitroacetanilide (4) is found to proceed with initial formation of a 1,3-disubstituted anionic σ-complex (II), which then reverts to the reactant system, relatively slowly giving N-alkyl-4-methoxy-(main product) and N-alkyl-2′-methoxy-4′,6′-dinitroacetanilides with the amido group unchanged, via a 1,4-disubstituted anionic σ-complex (III); kinetics and absorption and ¹H n.m.r. spectral data are reported.