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A Study on the reaction of heteroatom-stabilised carbanions with a, B- unsaturated ketones
Thesis (PhD )--University of Pretoria, 1997.
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| Format: | Thesis |
| Language: | English |
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University of Pretoria
2024
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| _version_ | 1867613688839536640 |
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| access_status_str | Open Access |
| author2 | Modro, T.A. |
| author_browse | Modro, T.A. |
| author_facet | Modro, T.A. |
| collection | Thesis |
| dc_rights_str_mv | © 2024 University of Pretoria. All rights reserved. The copyright in this work vests in the University of Pretoria. No part of this work may be reproduced or transmitted in any form or by any means, without the prior written permission of the University of Pretoria. |
| description | Thesis (PhD )--University of Pretoria, 1997. |
| format | Thesis |
| id | oai:repository.up.ac.za:2263/99461 |
| institution | University of Pretoria (South Africa) |
| language | English |
| last_indexed | 2026-06-10T12:40:07.894Z |
| license_str | Other — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UPSpace — University of Pretoria Institutional Repository |
| publishDate | 2024 |
| publishDateRange | 2024 |
| publishDateSort | 2024 |
| publisher | University of Pretoria |
| publisherStr | University of Pretoria |
| record_format | dspace |
| source_str | UPSpace — University of Pretoria Institutional Repository |
| spelling | oai:repository.up.ac.za:2263/99461 A Study on the reaction of heteroatom-stabilised carbanions with a, B- unsaturated ketones Modro, T.A. Pienaar, Andre Reaction Heteroatom-stabilised carbanions Bunsaturated ketones UCTD Thesis (PhD )--University of Pretoria, 1997. The methodology of the addition reactions of a wide range of alkyl- and arylmethylphosphonates to a,β-unsaturated ketones was studied. Reaction conditions were optimised and the conditions determining the nature of the addition, 1, 2- vs 1, 4-addition, were investigated. This was done in order to ascertain the specific conditions needed to determine the regioselectivity of these reactions. The I-hydroxy-alkyl- and 1-hydroxy-arylmethylphosphonates that were obtained, via 1, 2- addition, were used as substrates for further transformation reactions. The aromatisation of the hydroxyphosphonates was investigated. Three possible methods were implemented and the feasibility of these reactions in synthetic procedures was studied. The hydroxyphosphonates were transformed to their olefinic counterparts via dehydration under acidic conditions. These dehydration reactions were performed under kinetic as well as thermodynamic conditions and the relative stability of the different isomers was thus determined. The addition reaction of trimethylsilyl-stabilised carbanions to a,β-unsaturated ketones and saturated ketones was studied in an attempt to implement the Peterson olefination reaction sequence for the preparation of olefins. In the last chapter the synthetic procedures for the preparation of some substrates, needed during this study are discussed. Chemistry PhD 2024-11-27T09:15:55Z 2024-11-27T09:15:55Z 21/11/15 1997 Thesis http://hdl.handle.net/2263/99461 en © 2024 University of Pretoria. All rights reserved. The copyright in this work vests in the University of Pretoria. No part of this work may be reproduced or transmitted in any form or by any means, without the prior written permission of the University of Pretoria. application/pdf University of Pretoria |
| spellingShingle | Reaction Heteroatom-stabilised carbanions Bunsaturated ketones UCTD A Study on the reaction of heteroatom-stabilised carbanions with a, B- unsaturated ketones |
| title | A Study on the reaction of heteroatom-stabilised carbanions with a, B- unsaturated ketones |
| title_full | A Study on the reaction of heteroatom-stabilised carbanions with a, B- unsaturated ketones |
| title_fullStr | A Study on the reaction of heteroatom-stabilised carbanions with a, B- unsaturated ketones |
| title_full_unstemmed | A Study on the reaction of heteroatom-stabilised carbanions with a, B- unsaturated ketones |
| title_short | A Study on the reaction of heteroatom-stabilised carbanions with a, B- unsaturated ketones |
| title_sort | study on the reaction of heteroatom stabilised carbanions with a b unsaturated ketones |
| topic | Reaction Heteroatom-stabilised carbanions Bunsaturated ketones UCTD |
| url | http://hdl.handle.net/2263/99461 |