Kinetics of formation of zwitterionic complexes between 1,3,5-trinitrobenzene and diazabicyclo derivatives

Abstract

The title reactions are a simple model of nucleophilic attack of tertiary nitrogen on aromatic sp² carbons activated by the presence of nitro groups. The formation of the zwitterionic complexes is mildly affected by solvent changes and by addition of tetraethylammonium chloride. The reactivity of 1,4-diazabicyclo[2.2.2]octane, quinuclidine and 1,8-diazabicyclo[5.4.0]undec-7-ene is compared with that of primary and secondary amines.