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Triarylboranes in azo and carbene chemistry

Gazis, Theodore 2021. Triarylboranes in azo and carbene chemistry. PhD Thesis, Cardiff University.
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The overarching goal of this thesis is to explore the reactivity of several azo- containing compounds and iodonium ylides with fluorinated triarylboranes. An exhaustive study into reaction outcomes is envisaged by varying the fluorine substitution pattern on the triarylborane and hence, their Lewis acidity. To achieve this objective, state of the art analytical techniques such as multinuclear NMR spectroscopy, mass spectrometry, single crystal X-ray diffraction, and DFT calculations were utilised. Thus, valuable insights into the emerging and highly topical field of triarylborane azo and carbene activation would hopefully be achieved. In Chapter 3, the goal is to expose hydrazones and hydrazides to fluorinated triarylboranes under various reaction conditions. As a result, an assortment of dative and covalent N–N–B systems, including adducts, chain and heterocyclic compounds, are hoped to be furnished. Subsequently their structural properties will be thoroughly investigated. Chapter 4 aims to expand the reaction protocols developed in Chapter 3 to diaziridines. Firstly, the effect of triarylborane Lewis acidity and temperature will be explored to determine if divergent reactivity from Chapter 3 is observed. Secondly, Frustrated Lewis Pairs will be introduced to explore their potential in nitrogen activation and conversion. The impetus behind Chapter 5 is the transfer of aryl halogenated groups to acyclic diazo and iodonium ylide carbene precursors. Through a rare 1,3-carboboration a library of boron dienolates are expected to be furnished. Subsequently, their hydrolysis will be attempted as well as substrate scope expansion to cyclic iodonium ylides

Item Type: Thesis (PhD)
Date Type: Completion
Status: Unpublished
Schools: Chemistry
Date of First Compliant Deposit: 4 July 2022
Last Modified: 04 Jul 2022 11:37

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