This thesis has focussed on three main projects, all concerning electrophilic fluorination and fluorocyclization methodology. To begin with we considered the development of a novel fluoro-carbocyclization reaction, which combined the use of substrates of relatively low reactivity and rarely used carbon nucleophiles. Two major and common problems with electrophilic fluorination are the choice of a suitable reaction solvent and an appropriate fluorine source. These challenges were encountered and overcome to furnish a large library of cyclized products in excellent yields starting from indene and dihydronaphthalene class substrates. Our attempts to extend this methodology to an asymmetric variant using literature protocol for asymmetric fluorination were unsuccessful due to insufficient reactivity, which prompted us to investigate a new class of chiral reagents. Using the structural core of the widely used achiral reagent Selectfluor™, we prepared a variety of novel reagents which displayed greater fluorinating power than what is currently available in the literature. Finally, by combining the methodology for fluoro-carbocyclization with our selection of chiral reagents we were able to successfully achieve an unprecedented metal-free asymmetric fluoro-carbocyclization.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:645961 |
| Date | January 2013 |
| Creators | Wolstenhulme, Jamie R. |
| Contributors | Gouverneur, Veronique |
| Publisher | University of Oxford |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
| Source | http://ora.ox.ac.uk/objects/uuid:98f17fab-7bce-44b2-92b5-53cb61dd554e |
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