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Regioselective Synthesis of a Stereodefined Heterocyclic Push-Pull Alkene. 1H NMR Studies and Two-Dimensional TLC Illustrating Z/E Isomerization

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Zdravko Dzambaski

Center for Chemistry, ICTM,11000 Belgrade, Serbia and Montenegro

Rade Markovic , Marija Baranac and Vesna Jovanovic

Faculty of Chemistry, University of Belgrade, 11001 Belgrade, Serbia and Montenegro

J. Chem. Educ., 2004, 81 (7), p 1026

DOI: 10.1021/ed081p1026

Publication Date (Web): July 1, 2004

Abstract

Facile and direct regioselective synthesis of the 4-oxothiazolidine derivative from inexpensive chemicals as an example of kinetic versus thermodynamic control is described. The utility of ¹H NMR spectroscopy is illustrated as a tool to identify the configurational isomers. The role of solvent polarity on formation of intra- and intermolecular hydrogen bonds, which affect the configuration of the double bond in predictable way, is explained. In this sense an effective two-dimensional TLC serves as a analytical method to prove convincingly the Z/E isomerization of a fully delocalized trisubstituted exocyclic double bond. An application of the azeotropic mixture method for the preparation of one of the precursors in the synthesis of 4-oxothiazolidine derivative, emphasizes the educational significance of binary and tertiary azeotropes in practical organic synthesis. The experiment is suitable as a part of the upper-level organic chemistry laboratory course.