M. V. Pillai, K. Rajeswari, T. Vidhyasagar
Nov 5, 2014
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Citations
Journal
Journal of Molecular Structure
Abstract
Abstract A series of novel O -(Carboalkoxy)methyl oxime ether derivatives of 3-alkyl and 3,5-dialkyl-1-methyl-2,6-diphenylpiperidin-4-ones were synthesized and characterized through FT-IR, Mass, 1 H NMR, 13 C NMR, 1 H 1 H COSY, 1 H 13 C COSY and NOESY spectral techniques. The stereocontrolled formation of E -isomer exclusively in all the cases was confirmed by NMR spectral analysis. A 1,3 strain induced epimerization of C5 carbon in the case of compounds 18 and 23 was also observed. The preferred conformation of compounds 16 , 17 , 20 , 21 , 22 and 25 was found to be chair and for compounds 19 & 24 it was boat while compounds 18 and 23 adopt a twist boat conformation as observed by 1 H NMR and NOESY spectra. The solid state geometry of compound 16 was established by single crystal X-ray diffraction analysis.