Rate increase in consecutive nucleophilic aromatic substitution reactions of trichlorotrinitrobenzene: The synthesis of 1-(alkylamino)-3, 5-dichloro-2, 4, 6- …

…, A Zietsch, T Oeser, I Bolocan

Index: Wolff, J. Jens; Zietsch, Andreas; Oeser, Thomas; Bolocan, Ion Journal of Organic Chemistry, 1998 , vol. 63, # 15 p. 5164 - 5168

Full Text: HTML

Citation Number: 14

Abstract

The title compounds are formed by the nucleophilic aromatic substitution reaction between sym-trichlorotrinitrobenzene and amines. The yields and relative rates of formation depend critically on the degree of alkylation of the nucleophile. Contrary to the usual behavior, the introduction of a second and third donor is facilitated in the case of ammonia and monoalkylamines, while this is not the case for secondary amines. This behavior is ...