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Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles
Bibliography: pages 91-96.
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| Format: | Thesis |
| Language: | English |
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Department of Chemistry
2016
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| _version_ | 1867614380279988224 |
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| access_status_str | Open Access |
| author | Hendrickse, Theodore Franklin |
| author2 | Modro, Tomasz A |
| author_browse | Hendrickse, Theodore Franklin Modro, Tomasz A |
| author_facet | Modro, Tomasz A Hendrickse, Theodore Franklin |
| author_sort | Hendrickse, Theodore Franklin |
| collection | Thesis |
| description | Bibliography: pages 91-96. |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/17035 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:51:07.424Z |
| license_str | Not specified — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UCTD — University of Cape Town Open Access Repository |
| publishDate | 2016 |
| publishDateRange | 2016 |
| publishDateSort | 2016 |
| publisher | Department of Chemistry |
| publisherStr | Department of Chemistry |
| record_format | dspace |
| source_str | UCTD — University of Cape Town Open Access Repository |
| spelling | oai:open.uct.ac.za:11427/17035 Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles Hendrickse, Theodore Franklin Modro, Tomasz A Organic Chemistry Bibliography: pages 91-96. Different synthetic approaches to tertiary mixed phosphoric-carboxylic imides(III) are discussed. The preparation of (III) via the N-acylation of phosphoramidates was investigated. The reaction of PhC(O)X (X = Br, Cl, F) with the conjugate base of (EtO)₂P(O)NHMe (IX) yields three products: PhCO₂Et (4), PhC(O)NHMe (5) and (PhCO)₂NMe (6). (5) and (6) are formed via the initial rapid formation of (EtO)₂P(O)-NMe-C(O)Ph (IIIe), while (4) results from the E1cB related reaction of (EtO)₂P(O)NMe involving electrophilic assistance by PhC(O)X. The attack of various nucleophilic species at the mixed-imide (IIIe) was studied, and the possible mechanisms of the P-N bond cleavage, followed by the N-methyl transfer from the phosphoryl to the carbonyl centre are discussed. 2016-02-15T07:15:33Z 2016-02-15T07:15:33Z 1983 Master Thesis Masters MSc http://hdl.handle.net/11427/17035 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Organic Chemistry Hendrickse, Theodore Franklin Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles |
| thesis_degree_str | Master's |
| title | Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles |
| title_full | Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles |
| title_fullStr | Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles |
| title_full_unstemmed | Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles |
| title_short | Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles |
| title_sort | tertiary n acyl phosphoramidates a mechanistic study of their formation and collapse in reactions with nucleophiles |
| topic | Organic Chemistry |
| url | http://hdl.handle.net/11427/17035 |
| work_keys_str_mv | AT hendricksetheodorefranklin tertiarynacylphosphoramidatesamechanisticstudyoftheirformationandcollapseinreactionswithnucleophiles |