Abstract The reaction of 2, 4-dinitrohalobenzenes with di-isopropylamine produces mainly N- (2, 4-dinitrophenyl)-isopropylamine and N-(2, 4-dinitrophenyl)-n-propylamine instead of the expected straightforward substitution product. Dealkylations are also observed in the reactions with isopropylcyclohexylamine and dicyclohexylamine. A carbanionic mechanism is proposed.