The chemistry of 1,2-dihydro-1,2-azaborine and nitrated lipids
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Date
2010-09
Authors
Marwitz, Adam John Von, 1981-
Journal Title
Journal ISSN
Volume Title
Publisher
University of Oregon
Abstract
1,2-Dihydro-1,2-azaborine is a six-membered aromatic heterocycle that is related to the quintessential aromatic molecule, benzene, via the replacement of a CC fragment in benzene with an isoelectronic BN bond-pair. Like the benzene motif, 1,2-dihydro-1,2-azaborine derivatives could provide opportunities in fields ranging from medicine to materials. Recent breakthroughs in the synthesis of 1,2-dihydro-1,2-azaborine have led to a burgeoning interest in this relatively unexplored heterocycle. This dissertation describes the synthesis, characterization, and potential applications of novel 1,2-dihydro1,2-azaborines. Chapter I reviews the chemistry of monocyclic and polycyclic BN-heterocycles over the last fifty years. Chapter II introduces the synthesis of numerous boron-substituted 1,2-dihydro-1,2-azaborine derivatives from a versatile precursor. Chapter III discusses the first successful synthesis of the parent 1,2-dihydro-1,2-azaborine, which is isoelectronic with benzene itself. An examination of the chemistry of 1,2-dihydro-1,2-azaborine provides a direct comparison of its properties relative to benzene. Chapter IV discusses the synthesis and characterization of 1,2-dihydro-1,2-azaborines incorporated into phenylacetylenic scaffolds. Chapter V discusses unrelated work on nitrated lipids, which was performed under the guidance of Professor Bruce Branchaud. The chapter introduces the importance of nitrated lipids in a biological context and details the synthetic achievements in this field.
This dissertation includes previously published and unpublished co-authored material.
Description
xxv, 468 p. : ill. (some col.) A print copy of this thesis is available through the UO Libraries. Search the library catalog for the location and call number.
Keywords
Dihydro-1,2-azaborine, Nitrated lipids, Benzene, Aromatic heterocycle, Boron heterocycle, Conjugated organic materials, Chemistry, Biochemistry, Organic chemistry