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Synthetic and mechanistic investigations of superelectrophilic reactions

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dc.contributor.advisor Klumpp, Douglas A. en_US Boblak, Kenneth Nicholas en_US 2017-08-02T21:16:18Z 2017-08-02T21:16:18Z 2014
dc.description Advisors: Douglas A. Klumpp. en_US
dc.description Committee members: Marc J. Adler; Elizabeth R. Gaillard; Timothy J. Hagen; Linda S. Yasui. en_US
dc.description.abstract This dissertation describes various intramolecular cyclizations promoted by superacid. The first chapter deals with the formation of N-heterocyclic indenes. In these reactions protonated N-heterocyclic rings are shown to enhance the reactivity of the carboxonium electrophile for the cyclodehydration of various ketones. The second chapter explores an unusual regioelectronic effect that controls whether Markovnikov or conjugate addition takes place across a double bond. The addition facilitated by superacid depends on the position of olefin functionality on N-heterocyclic olefinic derivatives. The final chapter investigates highly stable superelectrophilic systems and the trapping of their carbocations to highly functionalized fluorenes. This study includes the direct observation of dicationic and tricationic reactive intermediates in magic acid media via low temperature, nuclear magnetic resonance spectroscopy. The superelectrophilic cores promote charge-charge repulsion enhancing anti-aromaticity of the polycyclic-fluorene protons. en_US
dc.format.extent 193 pages en_US
dc.language.iso eng en_US
dc.publisher Northern Illinois University en_US
dc.rights NIU theses are protected by copyright. They may be viewed from Huskie Commons for any purpose, but reproduction or distribution in any format is prohibited without the written permission of the authors. en_US
dc.subject.lcsh Superelectrophiles en_US
dc.subject.lcsh Organic compounds--Synthesis en_US
dc.subject.lcsh Organic chemistry en_US
dc.title Synthetic and mechanistic investigations of superelectrophilic reactions en_US
dc.type Text en_US
dc.contributor.department Department of Chemistry and Biochemistry en_US Ph.D. (Doctor of Philosophy) en_US

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