Fundamental Chemistry of 1,2-Dihydro-1,2-Azaborines
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Benzene and its derivatives are ubiquitous in chemical research, with applications ranging from material science to biomedical research. 1,2-Dihydro-1,2-azaborine is a benzene mimic which replaces a CC bond with a BN bond. The basic science and applications of 1,2-azaborines is relatively underdeveloped. This thesis expands the fundamental understanding of 1,2-azaborines. Chapter I describes the air and moisture stability of 1,2-azaborines. Chapter II introduces nucleophilic aromatic substitution reactions that the parent 1,2-dihydro-1,2-azaborine will undergo. Chapter III discusses a trimerization reaction that 1,2-dihydro-1,2-azaborine can perform, which is unique from benzene. Chapter IV examines a novel protection free synthesis of 1,2-azaborines, which provides a more direct route to functionalized 1,2-azaborines. Chapter V discusses the novel deprotection of the N-silicon using an amide, giving one of the first 1,2-azaborine pharmaceutical mimics. Finally, chapter VI summarized miscellaneous contributions I have made to the basic science of 1,2-azaborines. This dissertation includes previously published and unpublished co-authored material.