Note
Includes bibliography.
Member of
Contributors
Publisher
Florida Atlantic University
Date Issued
2014
EDTF Date Created
2014
Description
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 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.
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.
Language
Type
Genre
Form
Extent
32 p.
Identifier
FA00003613
Rights
Copyright © is held by the author, with permission granted to Florida Atlantic University to digitize, archive and distribute this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires permission of the copyright holder.
Additional Information
Includes bibliography.
Thesis (B.A.)--Florida Atlantic University, Harriet L. Wilkes Honors College, 2014.
Date Backup
2014
Date Created Backup
2014
Date Text
2014
Date Created (EDTF)
2014
Date Issued (EDTF)
2014
Extension
FAU
IID
FA00003613
Organizations
Attributed name: Harriet L. Wilkes Honors College
Person Preferred Name
Dombrowski, Thomas
Physical Description
born digital
32 p.
Title Plain
DIELS-ALDER REACTIONS OF IN SITU GENERA TED CYCLOPENTADIENE IN HYDROCARBON AND FLUOROUS SOL VENTS
Use and Reproduction
Copyright © is held by the author, with permission granted to Florida Atlantic University to digitize, archive and distribute this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires permission of the copyright holder.
Digital Origin
born digital
Origin Information
2014
2014
Florida Atlantic University
Boca Raton, Florida
Physical Location
Florida Atlantic University Libraries
Place
Boca Raton, Florida
Sub Location
Digital Library
Title
DIELS-ALDER REACTIONS OF IN SITU GENERA TED CYCLOPENTADIENE IN HYDROCARBON AND FLUOROUS SOL VENTS
Other Title Info
DIELS-ALDER REACTIONS OF IN SITU GENERA TED CYCLOPENTADIENE IN HYDROCARBON AND FLUOROUS SOL VENTS