Synthesis and reactivity of α-diazosulfoxide and α-diazosulfone derivatives

dc.check.date9999-01-01
dc.check.embargoformatE-thesis on CORA onlyen
dc.check.entireThesisEntire Thesis Restricted
dc.check.infoIndefiniteen
dc.check.opt-outNot applicableen
dc.check.reasonThis thesis is due for publication or the author is actively seeking to publish this materialen
dc.contributor.advisorMaguire, Anita R.en
dc.contributor.authorKelleher, Patrick G.
dc.date.accessioned2014-09-18T09:21:51Z
dc.date.issued2000
dc.date.submitted2000
dc.description.abstractThe research described in this thesis involves the synthesis of α-diazo-β-oxo sulfoxides, and exploration of their reactivity. The first chapter includes an introduction to diazocarbonyl chemistry, specifically focusing on the synthesis of diazo compounds, and diazosulfoxide derivatives. The chemistry of sulfines, in particular the generation of α-oxo sulfines and their subsequent trapping as cycloadducts and dimerisation is discussed. The results of this research are discussed in the second and third chapters. The design, synthesis and reactivity of α-diazo-β-oxo sulfoxides is described in chapter 2 where diazo transfer adjacent to sulfoxides to form stable α-diazo-β-oxo sulfoxides has been achieved in cyclic systems. Decomposition of theses α-diazosulfoxides using rhodium carboxylate or carboxamide catalysts is also described. These processes proceed via a Wolff type rearrangement to form α-oxo sulfine intermediates, which were trapped as cycloadducts with dienes. In the absence of a diene trap, dimerisation of the sulfine intermediate was observed. Intramolecular C-H insertion reasctios of α-diazo-α-sulfonyl esters to form substituted sulfolane esters is described in chapter 3. The reactivity of these sulfolane esters is briefly explored. The fourth chapter contains the experimental details and the spectral and analytical data for all new compounds reported.en
dc.description.statusNot peer revieweden
dc.description.versionAccepted Version
dc.format.mimetypeapplication/pdfen
dc.identifier.citationKelleher, P. G. 2000. Synthesis and reactivity of α-diazosulfoxide and α-diazosulfone derivatives. PhD Thesis, University College Cork.en
dc.identifier.urihttps://hdl.handle.net/10468/1666
dc.languageEnglishen
dc.language.isoenen
dc.publisherUniversity College Corken
dc.relation.urihttp://library.ucc.ie/record=b1315292~S0
dc.rights© 2000, Patrick G. Kelleheren
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/3.0/en
dc.subjectIntramolecular C-H insertion reactionsen
dc.subjectDesignen
dc.subjectSynthesisen
dc.subjectReactivityen
dc.subjectSulfoxidesen
dc.subjectDiazocarbonyl chemistryen
dc.subject.lcshChemistry, Organicen
dc.thesis.opt-outfalse
dc.titleSynthesis and reactivity of α-diazosulfoxide and α-diazosulfone derivativesen
dc.typeDoctoral thesisen
dc.type.qualificationlevelDoctoralen
dc.type.qualificationnamePhD (Science)en
ucc.workflow.supervisorcora@ucc.ie
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