Aromatic nucleophilic substitution (snar) reactions of halo‐substituted dinitrobenzene in liposome reaction media: Effect of reaction medium and role of halogen leaving group

Abstract

AbstractSNAr reactions constitute an important pathway for the synthesis of many crucial organic derivatives from polyhaloaromatic compounds. The sluggish nature of the reaction in many cases makes it a challenging pathway and limits its potential applications. In the present report, liposomes have been used as model membrane systems to study nucleophilic substitution reactions of halo‐substituted dinitrobenzene with morpholine. The results show an interesting dependence of the reactivity on the size and composition of liposomes. The extent of rate acceleration in liposomes is strongly dependent on the identity of the halogen which undergoes the substitution—for example, chloro‐substituted aromatic compounds show the most sensitivity to the presence of lipsomal reaction media. The observed behavior correlates with the reported reactivity of halobenzenes while revealing interesting details which may be critical in harnessing the reactivity of less reactive substrates. The results explore the viability of employing liposomes as promising alternatives for synthetic protocols.