Tetrahedron p. 2551 - 2556 (1997)
Update date:2022-08-30
Topics:
Kakanejadifard, Ali
Farnia, S. Morteza F.
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, n(N) → σ*(C-N) in N-C-N moieties manifested by reduction in N-pyramidality and short C-N bond lengths. Moreover, 1H-NMR studies showed the dependency of methylenic protons splitting pattern on solvent polarity.
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