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New and improved hydrogen isotope exchange reactions.

Cummins, Veronica Clare. (1998) New and improved hydrogen isotope exchange reactions. Doctoral thesis, University of Surrey (United Kingdom)..

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Compounds labelled with deuterium and tritium are widely used in the life sciences. Consequently there is always a need for improved methods - better incorporation, higher specificity, reduced reaction time etc. and in the case of tritium, less radioactive waste. This thesis is concerned with such aspects. Chapter 1 is a review of the background to tritium and current methods of labelling and analysis of hydrogen isotopes. In chapter 2 the possible use of an organometallic compound - the ruthenium dihydro complex, RuH2CO(PPh3)3, which is known to catalyse the insertion of olefins into the ortho position of aromatic ketones, is explored. Solid deuterated formates e.g. 2-naphthy methyl-d-formate and d-formanilide were prepared and these were used to make the deuterated complex, RuD2CO(PPh3)3 which was used to exchange deuterium into the ortho position of aromatic ketones. Aromatic compounds with other functionalities, however were not so amenable to labelling, aromatic amides were the only other compounds successfully labelled. The method is therefore more restrictive than was hoped. A method to prepare tritiated formates by ozonolysis of 2-[T]-5-phenyloxazole to a mixed anhydride followed by nucleophillic attack was discovered. [T]-formanilide was prepared in this way but only at low levels of radioactivity (0.1 Ci/mmol, 3.67 GBq/mmol) which prevented the tritiated complex being prepared. In chapter 3 the use of zeolites as strong acid catalysts for hydrogen isotope exchange reactions was explored. Isotope exchange was carried out on simple organic molecules using hydrogen, platinum and palladium exchanged zeolite-Y with D2O and HTO as isotope source. Some studies were also carried out using solid deuterium sources with the metal exchanged zeolites. Exchange occurred using 2-naphthgyl methyl-d-formate, tetrabutyl ammonium-d-formate and potassium-d-formate. In addition, microwave activation was used in order to reduce reaction times and improve isotopic incorporation.

Item Type: Thesis (Doctoral)
Divisions : Theses
Authors :
Cummins, Veronica Clare.
Date : 1998
Contributors :
Depositing User : EPrints Services
Date Deposited : 09 Nov 2017 12:14
Last Modified : 15 Mar 2018 21:17

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