The Diels-Alder reaction is one of the most powerful reactions available to synthetic chemists. Novel catalysts for this reaction are constantly being evaluated, thus creating a need for high-throughput assays. In this thesis, three strategies were tested in the design of novel fluorescence-based assays to monitor Diels-Alder reactions. The first strategy relied on intermolecular FRET pairing using fluorescence donors as dienes and fluorescence acceptors as dienophile (or vice versa). The second strategy utilized the dienophile naphthalene fumarate ethyl ester which contains a quenched fluorescent moiety. This dienophile was expected to regain its fluorescence upon Diels-Alder reaction with a diene. The third strategy involved a masked 7-hydroxycoumarin fluorophore linked to a dienophile. The fluorophore was positioned so that after Diels-Alder reaction it could be easily eliminated. The third strategy was the most promising even though several problems had to be overcome.
| Identifer | oai:union.ndltd.org:LACETR/oai:collectionscanada.gc.ca:QMM.81269 |
| Date | January 2004 |
| Creators | Caputo, Christine A. |
| Publisher | McGill University |
| Source Sets | Library and Archives Canada ETDs Repository / Centre d'archives des thèses électroniques de Bibliothèque et Archives Canada |
| Language | English |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Format | application/pdf |
| Coverage | Master of Science (Department of Chemistry.) |
| Rights | All items in eScholarship@McGill are protected by copyright with all rights reserved unless otherwise indicated. |
| Relation | alephsysno: 002179047, proquestno: AAIMR06379, Theses scanned by UMI/ProQuest. |
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