Date of Award

2014

Document Type

Dissertation/Thesis

Submission Date

October 2026

Thesis/Dissertation Advisor [Chair]

Dragojlovic, Veljko

Thesis/Dissertation Co-Chair

Smith, Eugene

Abstract

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.

Comments

Includes bibliography.

Extent

32 p.

Identifier

FA00003613

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