1. A1,3-strain mediated epimerization of 2e,3e,5e,6e-tetraarylpiperidin-4-one oximes
- Author
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Murugesan Srinivasan, S. Selvaraj, and S. Perumal
- Subjects
Magnetic Resonance Spectroscopy ,Strain (chemistry) ,Chemistry ,Stereochemistry ,Molecular Conformation ,Stereoisomerism ,General Chemistry ,Carbon-13 NMR ,Ring (chemistry) ,Oxime ,chemistry.chemical_compound ,Anti-Infective Agents ,Piperidines ,Oximes ,Proton NMR ,General Materials Science ,Epimer ,Two-dimensional nuclear magnetic resonance spectroscopy - Abstract
A series of tri- and tetraarylpiperidin-4-one oximes were synthesized from 2e,3e,6e-tri- and 2e,3e,5e,6e-tetraarylpiperidin-4-ones, respectively. In the case of the latter compounds, oximation is accompanied by epimerization at C-5 to avoid the A1,3-strain between the oxime OH group and the 5e-aryl ring of the initially formed oxime resulting in 2e,3e,5a,6e-tetraarylpiperidin-4-one oximes. 1H, 13C and 2D NMR spectroscopic data were employed to characterize and investigate the stereochemistry of these compounds. Copyright © 2004 John Wiley & Sons, Ltd.
- Published
- 2004