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2002
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February
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In the Laboratory
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The Microscale Laboratory
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Microscale Synthesis of a Diphenylisoxazoline by a 1,3-Dipolar Cycloaddition
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William B. Martin, Laura J. Kateley, Dawn C. Wiser, and Catherine A. Brummond
Department of Chemistry, Lake Forest College, Lake Forest, IL 60045-2399
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February 2002
Vol. 79 No. 2
p. 225
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| Abstract |
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This microscale synthesis of a diphenylisoxazoline gives students an opportunity to prepare and examine the heterocyclic product of a pericyclic 1,3-dipolar addition reaction analogous to a Diels-Alder reaction. Two reaction pathways are proposed, one leading to 3,4-diphenylisoxazoline and the other to 3,5-diphenylisoxazoline. The 1H NMR spectrum of the actual product is used to determine its structure and thus the reaction pathway. The proposed products have diasteriotopic hydrogens that are readily observed in the 1H NMR spectra. Molecular modeling also is used to predict which product is more probable and to offer a likely explanation for the regioselectivity of the reaction.
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| Supplement |
Student handouts for synthesis and molecular modeling, notes for the instructor, an NMR spectrum, and figures showing electron density surfaces are available.
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 Contents |
JCE2002p0225W folder containing two WordPerfect documents
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| Download |
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| More Information |
Citation |
Martin, William B.; Kateley, Laura J.; Wiser, Dawn C.; Brummond, Catherine A. J. Chem. Educ. 2002 79 225.
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Keywords |
Heterocycles; Laboratory Instruction; Microscale; Molecular Modeling / Dynamics; NMR Spectrometry; Organic Chemistry; Organic Synthesis; Pericyclic Reactions
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History |
Created:
Last Updated: |
January 2, 2002
March 16, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
2002
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February
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225
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