STUDIES OF THE SYNTHESIS, PROTONATION AND DECOMPOSITION OF 12-HEXAAZATETRACYCLO[5.5.0.0(5,9).0(3,11)]DODECANE (HBIW)

Reaction of glyoxal with benzylamine or with substituted benzylamines leads to the cage structure 3. The X-ray crystal structure of 3c forme d from 4-chlorobenzylamine is reported. H-1 and C-13 NMR spectra of 3a -j have been measured. Changes in spectra in the presence of acid indi cate successive reaction to give mono- and di-protonated species, 4 an d 5 respectively, in which the added protons bridge two nitrogen atoms . The kinetics of the decomposition of 3a in aqueous acetonitrile are compatible with two competing pathways involving reaction of the proto nated form with either water or more acid.