An investigation into reactivity and selectivity in cycloadditions of 1,3-dipoles with formamidines

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dc.contributor.advisor McCarthy, Daniel G. en
dc.contributor.author Brennan, Tina-Marie
dc.date.accessioned 2015-12-03T12:05:11Z
dc.date.issued 2015
dc.date.submitted 2015
dc.identifier.citation Brennan, T.-M. 2015. An investigation into reactivity and selectivity in cycloadditions of 1,3-dipoles with formamidines. PhD Thesis, University College Cork. en
dc.identifier.endpage 380
dc.identifier.uri http://hdl.handle.net/10468/2123
dc.description.abstract The objective of this research was to investigate the synthesis of nitrile oxides and to study their reactivity in 1,3-dipolar cycloadditions with formamidines. Chapter one looks at the literature surrounding the 1,3-dipolar cycloaddition reaction. It explores the generation of 1,3-dipoles (mainly nitrile oxides) and dipolarophiles (predominantly amidines). It discusses the potential synthetic uses of the 1,3-dipolar cycloadducts. It examines both and inter- and intra-molecular cycloaddition reactions. It recognises the use of the 1,3-dipolar cycloadditions as a successful method in building natural products and oxadiazolines. The decomposition of oxadiazolines as a route to nitriles is also outlined in this chapter. Chapter two discusses the results of this research candidate. The preparation of nitrile oxide precursors - hydroximoyl halides - is outlined at first. The generation of nitrile oxides is then demonstrated, followed by the preparation of furoxans. Methods for preparing the reference materials (nitriles and ureas), which result from decomposition of oxadiazolines, then follow. The preparation of series of Δ2-1,2,4- oxadiazolines via the 1,3-dipolar cycloaddition reaction is illustrated in this chapter. The selectivity of the addition of nitrile oxides to dipolarophiles was tested by competition reactions, which are also described in this chapter. NMR techniques were used in the study of the kinetics of the 1,3-dipolar cycloadditions used for the preparation of a series of Δ2-1,2,4-oxadiazolines, which is addressed in this chapter. Chapter three charts the experimental procedures followed to gain results which are discussed in chapter two. It also outlines all analytical data produced during the course of this research. en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher University College Cork en
dc.rights © 2015, Tina-Marie Brennan. en
dc.rights.uri http://creativecommons.org/licenses/by-nc-nd/3.0/ en
dc.subject Oxadiazoline en
dc.subject 1,3-dipolar cycloaddition en
dc.subject Nitrile oxide en
dc.subject Amidine en
dc.title An investigation into reactivity and selectivity in cycloadditions of 1,3-dipoles with formamidines en
dc.type Doctoral thesis en
dc.type.qualificationlevel Doctoral en
dc.type.qualificationname PhD (Science) en
dc.internal.availability Full text available en
dc.description.version Accepted Version
dc.contributor.funder Cork City Council en
dc.description.status Not peer reviewed en
dc.internal.school Chemistry en
dc.check.reason Releasing this thesis would cause substantial prejudice to the commercial interests of University College Cork en
dc.check.opt-out No en
dc.thesis.opt-out false
ucc.workflow.supervisor d.mccarthy@ucc.ie
dc.internal.conferring Autumn Conferring 2015


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