Reaction of 1, 3, 5-trinitrobenzene (TNB) with the malononitrile anion in methanol yields a carbon-bonded σ-adduct,(3). Ionisation of the remaining exocyclic hydrogen is favourable and yields the dianion (4). The initial reaction of 1-chloro-2, 4, 6-trinitrobenzene similarly occurs at an unsubstituted ring position, but is followed by slower nucleophilic attack at the 1- position yielding the substituted product. A major difference in the reaction of the ethyl ...
