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dc.contributor.advisorO'Hagan, David
dc.contributor.authorLaunay, Guillaume
dc.coverage.spatial241en_US
dc.date.accessioned2010-06-21T13:46:56Z
dc.date.available2010-06-21T13:46:56Z
dc.date.issued2010-06-23
dc.identifieruk.bl.ethos.552387
dc.identifier.urihttp://hdl.handle.net/10023/922
dc.description.abstractThe importance of fluorinated organic molecules has grown over the last 50 years, particularly in the pharmaceutical and agrochemical industries. Therefore the development of new methods for fluorination is a very attractive research area. In Chapter 1, the properties and impact of the fluorine atom on organic molecules are overviewed. Existing electrophilic and nucleophilic fluorination methods are reviewed, and new developments in asymmetric fluorination are discussed. The emergence of the Prins fluorination reaction as a side product in BF₃.OEt₂ catalysed processes has been investigated as a synthesis method in Chapter 2. Indeed, it is possible to form 4-fluorotetrahydropyrans with some diastereoselectivity from an allylic alcohol and an aldehyde with a stoichiometric amount of BF₃.OEt₂. During this study, formation of 4-fluoropiperidines from N-tosyl-4-butenylamine was achieved. Optimisation of reaction conditions was investigated such as the solvent, the reaction temperature and the influence of substituents on the alcohol and the aldehyde reagents. A ring-opening reaction of 4-fluoro-2-phenyltetrahydropyran was successfully performed. Both oxa-Prins and aza-Prins fluorination reactions were investigated under microwave conditions, allowing reduced reaction times, a process that had a minimum impact on the diastereoselectivity. Attempt to form γ-hydroxy-α-vinylfluorides by the reduction-fluorination of propargylic alcohols with aluminium hydride, or by Horner-Emmons reaction with diethyl (fluoromethyl)phosphonate are reported in Chapter 3. Unfortunately these approaches were unsuccessful in the preparation of γ-hydroxy-α-vinylfluorides. Attempts to fluorinate epoxides by α-lithiation and then treatment with electrophilic fluorination reagents gave encouraging results, but the products could not be purified and characterised due to an apparent instability.en_US
dc.language.isoenen_US
dc.publisherUniversity of St Andrews
dc.subjectFluorinationen_US
dc.subjectPrins reactionen_US
dc.subjectPiperidineen_US
dc.subjectPyranen_US
dc.subjectBF₃.OEt₂en_US
dc.subject.lccQD281.F55L2
dc.subject.lcshFluorinationen_US
dc.subject.lcshPrins reactionen_US
dc.subject.lcshPiperidineen_US
dc.subject.lcshPyranen_US
dc.titleNew approaches for C-F bond formation in organic chemistryen_US
dc.typeThesisen_US
dc.type.qualificationlevelDoctoralen_US
dc.type.qualificationnamePhD Doctor of Philosophyen_US
dc.publisher.institutionThe University of St Andrewsen_US


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