We use cookies to ensure that we give you the best experience on our website. By continuing to browse this repository, you give consent for essential cookies to be used. You can read more about our Privacy and Cookie Policy.

Durham e-Theses
You are in:

Nucleophilic substitution and cyclisation reactions of some polyfluoro-heteroaromatic and polyfluoroaromatic compounds

Drury, Christopher John (1994) Nucleophilic substitution and cyclisation reactions of some polyfluoro-heteroaromatic and polyfluoroaromatic compounds. Doctoral thesis, Durham University.



This thesis describes the reactions of some highly fluorinated aromatic and heteroaromatic compounds, in particular derivatives of naphthalene, quinoline and isoquinoline. Chapter 1 provides a general introduction to the preparation, reactions and applications of fluorine containing organic materials. Chapter 2 describes the reactions of some quinoline- and isoquinoline- thiolates with dimethyl acetylenedicarboxylate in an attempt to form six membered heterocycles. Chapter 3 describes nucleophilic substitution reactions of heptafluoro- quinoline and -isoquinoline with sulphur and oxygen nucleophiles. The sulphur nucleophiles are found to attack the 6- site in the isoquinoline and the 4- site in the quinoline. The oxygen nucleophiles attack the 1- site in the isoquinoline and 2- and 4- sites in the quinoline. Chapter 4 describes competition experiments of heptafluoro-quinoline and -isoquinoline with nucleophiles. Relative rates of attack at the 1- position and 6- position in the isoquinoline are determined for a variety of nucleophiles. The relative rates of two nucleophiles are determined for 4- attack in the quinoline. The relative reactivities of the two heterocycles are determined for two different nucleophiles. Chapter 5 describes the pyrolysis of heptafluoro-2-naphtiiyl propynoate which yield two difluoro-butenone derivatives. These decarbonylate under further pyrolysis to yield a 1,1-difluorocyclopropene. All the products were identified by X-ray crystallography. Chapter 6 gives experimental details for Chapter 2 to Chapter 5.

Item Type:Thesis (Doctoral)
Award:Doctor of Philosophy
Thesis Date:1994
Copyright:Copyright of this thesis is held by the author
Deposited On:16 Nov 2012 11:01

Social bookmarking: del.icio.usConnoteaBibSonomyCiteULikeFacebookTwitter