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Durham e-Theses
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Free radical syntheses of new organofluorine systems

Dunn, Stephen Norman (1996) Free radical syntheses of new organofluorine systems. Doctoral thesis, Durham University.



Use of the carbon hydrogen bond as a functional group in free radical addition reactions to fluoro - alkenes has been studied. Reactions involving additions of cyclic alcohols and cyclic as well as acyclic diols to hexafluoropropene, yielded selective hydroxyl group directed products in high yield. The subsequent alcohol or diol - hexafluoropropyl adducts were easily dehydrated using thionyl chloride and pyridine, forming alkenes and dienes containing a polyfluoroalkyl moety, in good yield. The resultant alkenes following bromination and epoxidation, were found to be electrophilic in nature. Furthermore, these alkenes were dehydrogenated using sulphur, yielding aromatic compounds containing the hexafluoropropyl moiety, in high yield. Additions of hydrocarbons to hexafluoropropene gave complex final mixtures, illustrating the poor selectivity of such reactions.

Item Type:Thesis (Doctoral)
Award:Doctor of Philosophy
Thesis Date:1996
Copyright:Copyright of this thesis is held by the author
Deposited On:09 Oct 2012 11:50

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