The photochemistry and 1,3-dipolar cycloadditions of 4-azidopyridine-N-oxide

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dc.contributor.advisor Poole, James S. en_US Hostetler, Katherine J. en_US 2011-06-03T19:40:32Z 2011-06-03T19:40:32Z 2005 en_US 2005
dc.identifier LD2489.Z78 2005 .H67 en_US
dc.description.abstract We have investigated the chemistry of 4-azidopyridine-N-oxide. One aspect of this thesis involved the photolysis of this azido heteroaromatic-N-oxide, to generate highly reactive nitrene intermediates. We have studied these intermediates and determined that the intermediates vary significantly in structure and reactivity from those of simpler phenyl and pyridyl systems. This study yields new insight into the structure, bonding, and energetics of nitrene species.The nitrene intermediate originating from this azide has features which could in the future help in synthetic practices and photoaffinity studies. It may aid in photoaffinity studies due to the fact that the N-oxide group imparts water solubility.This thesis investigates the premise that a change in the electronic nature of the aromatic ring results in a change in the systems reactivity. We are interested in whether changes in the nature of the ring in the azides induce large changes in the chemistry, and if so, whether they do so in a predictable manner.Another focus of the research involved 1,3-dipolar cycloaddition reactions with an azide, where a carbon-carbon double or triple bond will attach to an aromatic azide, 4-azidopyridine-N-oxide in this case, at the azido group (-N3) to generate new ring compounds. 1,3-dipolar cycloadditions are fascinating because the mechanism which takes place in the attachment phase is still under debate. These reactions were investigated by reacting 4-azidopyridine-N-oxide with an unsaturated compound (alkene or alkyne) and then analyzing the product mixtures by HPLC methods.
dc.description.sponsorship Department of Chemistry
dc.format.extent v, 104 leaves : ill. (some col.) ; 28 cm. en_US
dc.source Virtual Press en_US
dc.subject.lcsh Azides. en_US
dc.subject.lcsh Pyridine. en_US
dc.subject.lcsh Nitrenes. en_US
dc.title The photochemistry and 1,3-dipolar cycloadditions of 4-azidopyridine-N-oxide en_US Thesis (M.S.)
dc.identifier.cardcat-url en_US

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  • Master's Theses [5510]
    Master's theses submitted to the Graduate School by Ball State University master's degree candidates in partial fulfillment of degree requirements.

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