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Inter- and Intramolecular Ring-Opening Reactions of Oxabicyclic Substrates.

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Title: Inter- and Intramolecular Ring-Opening Reactions of Oxabicyclic Substrates.
Author: Wicks, Christopher
Department: Department of Chemistry
Program: Chemistry
Advisor: Tam, William
Abstract: Oxabenzonorbornadiene (OBD) and derivatives thereof have become key substrates of interest within synthetic organic chemistry and natural product synthesis as they enable the formation of multiple stereocenters in a single transformation. The present work expands on previous studies to investigate various intramolecular transformations, and regiochemical implications regarding ring-opening reactions of asymmetric oxabicyclic alkenes. Acid-catalyzed intramolecular ring-opening reactions of cyclopropanated oxabenzonorbornadiene (CPOBD) derivatives were investigated to afford novel medium-sized ring systems in moderate to good yields and good to excellent regioselectivity. Similarly, a Ni catalyzed intramolecular ring-opening reaction of alkyl halide tethered OBD compounds was optimized, thus generating a naphthalene derivative in excellent yields. Lastly, iridium-catalyzed ring-opening reactions of unsymmetrical C1-substituted OBD derivatives is presented using alcohols and water as nucleophiles which allows for the selective synthesis of previously inaccessible substrates.
Date: 2019-08
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Embargoed Until: 2020-08-02

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