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Aspects of organic synthesis using phosphorus derivatives

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posted on 19.07.2018 by M.F.S. Matough
Part 1. A mild, one-stage process has been developed for the preparation of primary and secondary alkyl chlorides by the reaction of the corresponding alcohols with phosphororus trisdimethylamide and carbon tetrachloride. In particular in this work the stability of common sugar protecting groups towards the reagent was examined. A number of model compounds containing acetal, ether or ester groups in addition to free hydroxyl group were examined. They were found to undergo a smooth conversion of hydroxyl to halide with no effect on other groups in the molecule. This rapid, high yield reaction proceeds with inversion of configuration and without evidence of isomerisation. The mechanism of the reaction and its extension to include other polyhalogenated hydrocarbons are discussed. For example by using bromoform or carbon tetrabromide the method has been extended to the synthesis of alkyl bromides. Part 2. The reaction of tertiary phosphine oxide anions with carbonyl compounds discovered by Horner et al. has been used in attempts to extend it for the preparation of phosphinic acids especially unsymmetrical phosphinic acids. The method was found to be of limited application.

Funding

Libya, Government (research studentship).

History

School

  • Science

Department

  • Chemistry

Publisher

© M.F.S. Matough

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

1968

Notes

A Doctoral Thesis. Submitted in partial fulfilment of the requirements for the award of Doctor of Philosophy at Loughborough University.

Language

en

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