Dual reactivity of 1-chloro- and 1-bromo-3,5-dinitrobenzenes in aromatic nucleophilic substitution

摘要

Aromatic nucleophilic substitution reactions in 1-halo-3,5-dinitrobenzenes (where the halogen is bromine or chlorine) can occur with replacement of either a nitro group or a halogen atom, depending on the nature of anionic nucleophile Nu(-) as a Lewis base (hard, soft or intermediate), as well as on the polarity of the dipolar aprotic solvent.