Tetrahedron Letters

Unusual dealkylations and rearrangements in aromatic nucleophilic substitution

NS Nudelman, SE Socolovsky

Index: Nudelman, N. Sbarbati; Socolovsky, S. E. Tetrahedron Letters, 1980 , vol. 21, p. 3331 - 3334

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Abstract

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.