Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles

Simple item page
dc.contributor.advisorModro, Tomasz Aen_ZA
dc.contributor.authorHendrickse, Theodore Franklinen_ZA
dc.date.accessioned2016-02-15T07:15:33Z
dc.date.available2016-02-15T07:15:33Z
dc.date.issued1983en_ZA
dc.descriptionBibliography: pages 91-96.en_ZA
dc.description.abstractDifferent 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.en_ZA
dc.identifier.apacitationHendrickse, T. F. (1983). <i>Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles</i>. (Thesis). University of Cape Town ,Faculty of Science ,Department of Chemistry. Retrieved from http://hdl.handle.net/11427/17035en_ZA
dc.identifier.chicagocitationHendrickse, Theodore Franklin. <i>"Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles."</i> Thesis., University of Cape Town ,Faculty of Science ,Department of Chemistry, 1983. http://hdl.handle.net/11427/17035en_ZA
dc.identifier.citationHendrickse, T. 1983. Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles. University of Cape Town.en_ZA
dc.identifier.ris TY - Thesis / Dissertation AU - Hendrickse, Theodore Franklin AB - 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. DA - 1983 DB - OpenUCT DP - University of Cape Town LK - https://open.uct.ac.za PB - University of Cape Town PY - 1983 T1 - Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles TI - Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles UR - http://hdl.handle.net/11427/17035 ER - en_ZA
dc.identifier.urihttp://hdl.handle.net/11427/17035
dc.identifier.vancouvercitationHendrickse TF. Tertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophiles. [Thesis]. University of Cape Town ,Faculty of Science ,Department of Chemistry, 1983 [cited yyyy month dd]. Available from: http://hdl.handle.net/11427/17035en_ZA
dc.language.isoengen_ZA
dc.publisher.departmentDepartment of Chemistryen_ZA
dc.publisher.facultyFaculty of Scienceen_ZA
dc.publisher.institutionUniversity of Cape Town
dc.subject.otherOrganic Chemistryen_ZA
dc.titleTertiary N-acyl phosphoramidates : a mechanistic study of their formation and collapse in reactions with nucleophilesen_ZA
dc.typeMaster Thesis
dc.type.qualificationlevelMasters
dc.type.qualificationnameMScen_ZA
uct.type.filetypeText
uct.type.filetypeImage
uct.type.publicationResearchen_ZA
uct.type.resourceThesisen_ZA
Files
Original bundle
Now showing 1 - 1 of 1
Thumbnail Image
Name:
thesis_sci_1983_hendrickse_theodore_franklin.pdf
Size:
1.81 MB
Format:
Adobe Portable Document Format
Description:
Download
Collections
Masters