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NMR study of the stereochemistry of 2,4,6,8‐tetraaryl‐3,7‐diazabicyclo[3.3.1]nonan‐9‐ones
Author(s) -
Vijayakumar V.,
Sundaravadivelu M.,
Perumal S.,
Hewlins M. J. E.
Publication year - 2000
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/1097-458x(200010)38:10<883::aid-mrc708>3.0.co;2-v
Subject(s) - chemistry , chemical shift , aryl , carbon 13 nmr , proton nmr , nuclear overhauser effect , stereochemistry , two dimensional nuclear magnetic resonance spectroscopy , spectral line , nuclear magnetic resonance spectroscopy , nuclear magnetic resonance , organic chemistry , alkyl , physics , astronomy
The 1 H and 13 C NMR spectra of 2,4,6,8‐tetraaryl‐3,7‐diazabicyclo[3.3.1]nonan‐9‐ones were measured at 360 and 90 MHz, respectively. The chemical shifts were assigned unambiguously using one‐ and two‐dimensional NMR spectroscopic data and nuclear Overhauser enhancement studies. These results clearly indicate a chair–boat conformation for these compounds with (i) all aryl groups orientated equatorially and (ii) the aryl groups of the boat lying in the shielding zone of the aryl groups of the chair. Literature assignments of carbon chemical shifts were also revised. Copyright © 2000 John Wiley & Sons, Ltd.