A Study of Intermolecular and Intramolecular Horner-Wadsworth-Emmons Olefination of Substituted5-(Diethoxyphosphoryl)-N-acylpiperidin-4-ones

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dc.contributor.advisorDr. Daniel L. Comins, Chairen_US
dc.contributor.advisorDr. Suzanne T. Purrington, Memberen_US
dc.contributor.advisorDr. Binghe Wang, Memberen_US
dc.contributor.authorOllinger, Christian G.en_US
dc.date.accessioned2010-04-02T18:03:15Z
dc.date.available2010-04-02T18:03:15Z
dc.date.issued2000-07-31en_US
dc.degree.disciplineChemistryen_US
dc.degree.levelMaster's Thesisen_US
dc.degree.nameMSen_US
dc.description.abstractThis research has focused on extending the utility of previously synthesized 5-iodo-2,3-dihydro-4-pyridones. The initial conversion involved introducing a phosphonate group by nickel-catalyzed cross-coupling with the vinyl iodide at the C-5 position. Using a Horner-Wadsworth-Emmons reaction, the phosphonate ester was then converted to various olefins in moderate to high yields. Having an aldehyde present on the substituted 5-(diethoxyphosphoryl)--acylpiperidin-4-one allowed cyclization to occur thereby providing a bicyclic enone.en_US
dc.identifier.otheretd-20000729-112252en_US
dc.identifier.urihttp://www.lib.ncsu.edu/resolver/1840.16/1328
dc.rightsI hereby certify that, if appropriate, I have obtained and attached hereto a written permission statement from the owner(s) of each third party copyrighted matter to be included in my thesis, dissertation, or project report, allowing distribution as specified below. I certify that the version I submitted is the same as that approved by my advisory committee. I hereby grant to NC State University or its agents the non-exclusive license to archive and make accessible, under the conditions specified below, my thesis, dissertation, or project report in whole or in part in all forms of media, now or hereafter known. I retain all other ownership rights to the copyright of the thesis, dissertation or project report. I also retain the right to use in future works (such as articles or books) all or part of this thesis, dissertation, or project report.en_US
dc.titleA Study of Intermolecular and Intramolecular Horner-Wadsworth-Emmons Olefination of Substituted5-(Diethoxyphosphoryl)-N-acylpiperidin-4-onesen_US

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