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1H and 13C NMR spectral study of some 3-aryl-5r-aryl-6t-carbethoxycyclohex-2-enones—a study of four-bond 1H1H couplings

✍ Scribed by C. Yuvaraj; K. Pandiarajan

Publisher
John Wiley and Sons
Year
2011
Tongue
English
Weight
138 KB
Volume
49
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Nine 3‐aryl‐5__r__‐aryl‐6__t__‐carbethoxycyclohex‐2‐enones 2a–2i have been synthesized. For all these compounds, ^1^H and ^13^C NMR spectra have been recorded. For two compounds, 2D spectra have been recorded. The spectral data suggest that these compounds adopt sofa conformation in solution with H‐5, H‐6 and H‐4__t__ occupying axial‐like positions and H‐4__c__ occupying equatorial‐like positions. In 3‐phenyl‐5__r__‐(o‐chlorophenyl)‐6__t__‐carbethoxycylohex‐2‐enone (2b), the o‐chlorophenyl group is oriented such that the chlorine atom is in between H‐4__c__ and H‐5. Allylic coupling of H‐2 is observed only with H‐4__t__. Evidence has been obtained for four‐bond coupling between 1,3‐diaxial and 1,3‐axial–equatorial protons. Copyright © 2011 John Wiley & Sons, Ltd.

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