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2004
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In the Laboratory
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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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Rade Marković, Marija Baranac, and Vesna Jovanović
Faculty of Chemistry, University of Belgrade, 11001 Belgrade, Serbia and Montenegro
Zdravko Džambaski
Center for Chemistry, ICTM,11000 Belgrade, Serbia and Montenegro
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July 2004
Vol. 81 No. 7
p. 1026
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| Abstract |
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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.
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| Supplement |
Student handout, instructor's notes, spectral data, and information on the hazards of the chemicals used in the experiment are available.
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 Contents |
JCE2004p1026W.doc (Microsoft Word)
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| More Information |
Citation |
Marković, Rade; Baranac, Marija; Jovanović, Vesna; Džambaski, Zdravko. J. Chem. Educ. 2004 81 1026.
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Keywords |
Heterocycles; Laboratory Instruction; NMR Spectrometry; Organic Chemistry; Organic Synthesis; Stereochemistry
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History |
Created:
Last Updated: |
May 27, 2004
January 19, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
2004
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July
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1026
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