H-1 and C-13 NMR spectral assignments of some novel 2,4,6,8-tetraaryl-3,7-diazabicyclo[3.3.1]nonan-9-one derivatives

摘要

The H-1 and C-13 NMR spectra of 2,4,6,8-tetraaryl-3,7-diazabicyclo[3.3.1]nonan-9-ones (1-2),oximes (3-8) and O-benzyl oximes (9-12) were recorded. The chemical shifts were unambiguously assigned using 1D and 2D NMR spectral data. The results clearly indicate that the compounds exist in chair-boat conformation with equatorial and axial orientation of the aryl groups in the chair and boat forms, respectively. Since the molecules are flexible and dynamic in solution, the chair and boat forms are mutually interconvertible. In 3-12, because of the effect of oximation/oximination, all the protons in the heterobicyclic systems gave distinct signals except the benzylic protons of the boat form. In all synthesized compounds, the aryl group protons at C-6,8 are shielded by the aryl groups at C-2,4 and therefore appear in the lower frequency region than the aryl groups at C-2,4. Copyright (C) 2008 John Wiley & Sons, Ltd.