Current Search: Dragojlovic, Veljko (x) » Dombrowski, Thomas (x)
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Title
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DIELS-ALDER REACTIONS OF IN SITU GENERA TED CYCLOPENTADIENE IN HYDROCARBON AND FLUOROUS SOL VENTS.
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Creator
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Dombrowski, Thomas, Dragojlovic, Veljko, Smith, Eugene, Harriet L. Wilkes Honors College
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Abstract/Description
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The stereoselectivity ofthe Diels-Alder reaction of cyclopentadiene and maleic anhydride towards its exo adduct was improved in perfluorinated solvents, in comparison to a reaction carried out in hydrocarbon solvents and a solvent free reaction. When using FC-70, the reaction of in situ generated cyclopentadiene and maleic anhydride produced exo- norbomene-cis-5,6-dicarboxylic anhydride and endo- norbomene-cis-5,6- dicarboxylic anhydride in a ratio of 52:32 according to GC-MS analysis. In...
Show moreThe stereoselectivity ofthe Diels-Alder reaction of cyclopentadiene and maleic anhydride towards its exo adduct was improved in perfluorinated solvents, in comparison to a reaction carried out in hydrocarbon solvents and a solvent free reaction. When using FC-70, the reaction of in situ generated cyclopentadiene and maleic anhydride produced exo- norbomene-cis-5,6-dicarboxylic anhydride and endo- norbomene-cis-5,6- dicarboxylic anhydride in a ratio of 52:32 according to GC-MS analysis. In hydrocarbon solvent, mesitylene, the ratio of exo/endo was found to be 23:52, indicating a more kinetically-controlled reaction. Separation of the reaction products by radial chromatography provided the endo adduct in 89% purity and the exo adduct in 47% purity.
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Date Issued
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2014
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PURL
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http://purl.flvc.org/fau/fd/FA00003613
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Format
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Document (PDF)