C. Boga et L. Forlani, KINETICS OF FORMATION OF ZWITTERIONIC COMPLEXES BETWEEN 1,3,5-TRINITROBENZENE AND DIAZABICYCLO DERIVATIVES, Journal of the Chemical Society. Perkin transactions. II (Print), (10), 1998, pp. 2155-2157
The title reactions are a simple model of nucleophilic attack of terti
ary nitrogen on aromatic sp(2) carbons activated by the presence of ni
tro groups. The formation of the zwitterionic complexes is mildly affe
cted 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.