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Volume 20 (2006), Issue 3, Pages 95-107

Determination of the enantiomeric composition of chiral delta-2-thiazolines-1,3 by 1H and 19F NMR spectroscopy using chiral solvating agents

Bérangère Merelli, Laurence Menguy, Estelle Soubeyrand-Lenoir, and Jean-Claude Cherton

Institut Lavoisier (UMR 8180), Université de Versailles Saint-Quentin en Yvelines, 45 Avenue des Etats-Unis 78035, Versailles Cedex, France

Copyright © 2006 Hindawi Publishing Corporation. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


Studies of the perturbing effect of chiral solvating agents (CSAs) namely the fluoroalcohols 5a and 5b upon the NMR spectra of chiral Δ2-thiazolines 1 presenting interesting insecticidal properties demonstrated the ability of these CSAs to afford diastereomeric solvates from these substrates providing their enantiomeric discrimination. Thus, for five of the six tested Δ2-thiazolines 1A and 1B there is at least one possibility to proceed to their enantiomeric discrimination either by 1H or 19F NMR using mostly 5b as CSA.