Abstract
The condensation of aniline with glyoxal and formaldehyde in stoichiometric ratio, leads to 2,4,6,8-tetraphenyl-2,4,6,8-tetraazabicyclo[3.3.0]octane (1f) with formic acid as catalyst. Nine substituted derivatives of 1f have been prepared in high yield by this synthetic method. X-ray analysis revealed the existence of an anomeric effect, nN → σC-N∗ in N-C-N moieties manifested by reduction in N-pyramidality and short CN bond lengths. Moreover, 1H-NMR studies showed the dependency of methylenic protons splitting pattern on solvent polarity.
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