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1997
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November
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In the Laboratory
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Epoxidation of Geraniol: An Advanced Organic Experiment that Illustrates Asymmetric Synthesis
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Lynn M. Bradley, Joseph W. Springer, Gregory M. Delate, and Andrew Goodman
The College of New Jersey, Department of Chemistry, Hillwood Lakes, CN 4700, Trenton, NJ 08650-4700
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November 1997
Vol. 74 No. 11
p. 1336
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| Abstract |
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The Sharpless epoxidation reaction is considered one of the most powerful advances in asymmetric organic synthesis (1). It is a classic example of the use of an asymmetric catalyst to provide an enantiomerically enriched mixture of epoxy alcohols. The procedure typically uses titanium(IV) tetraisopropoxide (Ti(OiPr)4) as a catalyst, a peroxide, and dialkyl tartrates to induce asymmetry in the epoxidation reaction of allylic alcohols. The experiment described in this paper illustrates the principle of asymmetric epoxidation and enables students to determine enantiomeric product ratios using chiral shift reagents and NMR spectroscopy.
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| More Information |
 Citation |
Bradley, Lynn M.; Springer, Joseph W.; Delate, Gregory M.; Goodman, Andrew. J. Chem. Educ. 1997 74 1336.
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Keywords |
Laboratory Instruction, Organic Chemistry, Chromatography, NMR Spectrometry, Organic Synthesis, and Stereochemistry
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History |
Created:
Last Updated: |
July 26, 1999
June 23, 2005
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| Home > JCE Print > Journal of Chemical Education > Issues >
1997
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November
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1336
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