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A 1,3 ‐strain mediated epimerization of 2e,3e,5e,6e‐tetraarylpiperidin‐4‐one oximes
Author(s) -
Srinivasan M.,
Perumal S.,
Selvaraj S.
Publication year - 2004
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/mrc.1480
Subject(s) - chemistry , epimer , oxime , stereochemistry , strain (injury) , ring (chemistry) , aryl , medicinal chemistry , organic chemistry , alkyl , medicine
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 A 1,3 ‐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. 1 H, 13 C and 2D NMR spectroscopic data were employed to characterize and investigate the stereochemistry of these compounds. Copyright © 2004 John Wiley & Sons, Ltd.