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A1,3-strain mediated epimerization of 2e,3e,5e,6e-tetraarylpiperidin-4-one oximes

✍ Scribed by M. Srinivasan; S. Perumal; S. Selvaraj

Book ID: 102530401
Publisher: John Wiley and Sons
Year: 2004
Tongue: English
Weight: 98 KB
Volume: 42
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1480

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✦ Synopsis

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 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.

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