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Metal-Mediated Transformations of Strained Intermediates

Abstract

This dissertation describes the study of metal-mediated transformations of strained cyclic alkynes and their applications to synthetic organic chemistry. Strained cyclic alkynes are in situ generated, fleeting intermediates with strain energies ranging from 40–50 kcal/mol. Harnessing the reactivity of these strained molecules, while challenging in many cases, offers a means to form multiple bonds in a single step, and generate products that may be inaccessible by other means. Herein, several synthetic endeavors are described that leverage strain release to advance our understanding of chemical reactivity and gain new entryways into important classes of organic and organometallic compounds. Finally, this dissertation describes a study towards the development of marijuana breathalyzer technology, which focuses on performing electrochemical oxidations of THC at low concentrations.

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