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Stereoselective synthesis through the activation of small rings

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thesis
posted on 02.08.2018 by Jaime Cummins
This thesis describes the use of both, a carbanion Payne-type rearrangement and η4-dienyl and η5-pentadienyl iron tricarbonyl complexes in organic chemistry. A carbanion Payne-type rearrangement has been developed and its reactivity investigated, with the subsequent trapping of a series of aldehydes or imines. The results are disappointing with no desired tetrahydrofuran-, tetrahydropyran- or pyrrolidine-containing molecules synthesised, although reasons for this are discussed. A novel 1,3-dipole containing a η5-iron tricarbonyl pentadienyl complex was synthesised on opening of a cyclopropane, subsequently trapping with a series of aldehyde and imines to efficiently form tetrahydrofuran and pyrrolidine ring structures, respectively. [Continues.]

Funding

Prosidion Ltd (project studentship).

History

School

  • Science

Department

  • Chemistry

Publisher

© Jaime Cummins

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

2006

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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