A(1,3)-strain mediated epimerization of 2e,3e,5e,6e-tetraarylpiperidin-4-one oximes.
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. 1H, 13C and 2D NMR spectroscopic data were employed to characterize and investigate the stereochemistry of these compounds.
Srinivasan
M
M
Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India.
Perumal
S
S
Selvaraj
S
S
D000890:Anti-Infective Agents / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010091:Oximes / Q000138:chemical synthesis*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000890:Anti-Infective Agents; D010091:Oximes; D010880:Piperidines