Date of Completion

5-7-2015

Embargo Period

4-24-2015

Keywords

Organic Chemistry; Synthetic Methodology; Reaction Development; Continuous Flow; Organofluorine; Oxoammonium Salt

Major Advisor

Dr. Nicholas E. Leadbeater

Associate Advisor

Dr. William F. Bailey

Associate Advisor

Dr. Mark W. Peczuh

Associate Advisor

Dr. Edward J. Neth

Field of Study

Chemistry

Degree

Doctor of Philosophy

Open Access

Campus Access

Abstract

This dissertation focuses on three areas for methods development: continuous-flow processing, oxoammonium salt-mediated transformations, and organofluorine-focused reactions. These areas are not only highly attractive to elements within the chemical community but represent a central theme in my work. Described herein, is the development of methods to perform metal-catalyzed reactions involving gaseous reagents (CO and H2) in continuous-flow reactors. In addition, the repertoire of oxidative protocols has been augmented to extend the frontier of oxoammonium salt-based transformations. Finally, a novel route to prepare trifluoromethyl cyclopropanes utilizing 1,3 g-silyl elimination was developed to advance organofluorine methodologies. The guiding principal behind this transformation, namely the enhanced neighboring group participation, has been expanded to synthesize fluoroalkyl- and perfluoroalkyl-substituted vinyl cyclopropanes.

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