A kinetic study of the reaction of N-n-butyl-2,6-dinitroaniline 1 with NaOH was carried out in 10% 1,4-dioxane–water at 25 °C, giving 2,6-dinitrophenol 2 and 7-nitro-2-n-propyl-1H-benzimidazole 3-oxide 3 in ratios depending on the HO−concentration. The rate constant for the formation of 2 is second order in HO− concentration while that of 3 is first order then, the relative amount of 2 ∶ 3 formed increases with HO−. A mechanism involving the formation of a σ complex by addition of HO− to an unsubstituted position of the aromatic ring is proposed for 2,6-dinitrophenol
formation. The mechanism suggested for the formation of the N-oxide requires the deprotonation of the substrate.
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