Show simple item record

Files in this item


There are no files associated with this item.

Item metadata

dc.contributor.authorDurie, Alastair J.
dc.description.abstractHighly polar organic fluorinated motifs are of interest in materials chemistry, for example, in liquid crystal applications. Cyclohexane is an important and widely used structural motif within organic chemistry. Work has been carried out to prepare single stereoisomers of multivicinal fluorinated cyclohexanes, a class of compounds that has not been previously produced. A synthesis of the all-syn-1,2,3,4-tetrafluorocyclohexane, in 9 steps from cyclohexa-1,3-diene will be presented. The ¹⁹F NMR spectra of the all-syn-1,2,3,4-tetrafluorocyclohexane shows interesting dynamic conformational effects. This is a small polar organic molecule, which was crystalline at room temperature. The structure of the compound was confirmed by single crystal X-ray diffraction studies. The synthesis of the all-syn-1,2,4,5-tetrafluorocyclohexane from cyclohexa-1,4-diene is also presented. The synthesis of a single diastereoisomer of 1,2,3,4,5,6-hexafluorocyclohexane, derived from benzene in 5 steps, is presented. As with the tetrafluoro compounds, the ¹⁹F NMR spectra of this compound shows dynamic conformational effects. The structure of the compound was confirmed by single crystal X-ray diffraction studies. The 1,2,4,5-tetrafluorocyclohexane motif was elaborated to contain a phenyl group, producing “rod-like” molecules. This motif was synthesised in view of potential applications for liquid crystalline materials.en_US
dc.publisherUniversity of St Andrews
dc.titleMultivicinal fluorine substitution of the cyclohexane ringen_US
dc.contributor.sponsorEngineering and Physical Sciences Research Council (EPSRC)en_US
dc.type.qualificationnamePhD Doctor of Philosophyen_US
dc.publisher.institutionThe University of St Andrewsen_US
dc.rights.embargodateElectronic copy restricted until 15 April 2016en_US
dc.rights.embargoreasonElectronic thesis unavailable: permission not provided to allow public accessen_US

This item appears in the following Collection(s)

Show simple item record