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Title: Stereochemistry of N-formyl-cis-2,4-diaryl-3-azabicyclo[3.3.1]nonanes
Authors: Jeyaraman, R
Thenmozhiyal, J C
Murugadoss, R
Venkatraj, M
Laavanya, P
Panchanatheswaran, K
Bhadbhade, M
Issue Date: Jul-2000
Publisher: NISCAIR-CSIR, India
Abstract: Four N-formyl-cis-2,4-diaryl-3-azabicyclo[3.3.1]nonanes 5-8 have been prepared and their preferred conformations determined using NMR spectral studies, X-ray crystallography and semiempirical calculations (AM1 and PM3 of MOPAC 6). They all prefer twin-chair conformation with a nearly coplanar N-CHO function with reference to the C2-N3-C4 plane. X-Ray analysis of a single crystal of 6 shows that there are two independent molecules in the asymmetric unit, the overall conformation being the same in both the molecules of the asymmetric unit. Employing variable temperature NMR studies, the barrier for N-C rotation in the N-formylazabicyclo[3.3.1]nonane 6 has been found to be 58.25 kJ/mol.
Page(s): 497-503
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.39B(07) [July 2000]

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