Developments in C-H oxidation methodologies

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Finney, Laura (2019) Developments in C-H oxidation methodologies. PhD thesis, University of Nottingham.

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Abstract

Chapter One of this thesis describes classical oxidation methodologies and the importance of the development of sustainable methodologies. The overall thesis aims are also outlined in relation to this.

In Chapter Two, cross-dehydrogenative coupling reactions to form benzylic C-C bonds are investigated with photo-activated 1,4-hydroquinone (BQH2). A review of the relevant literature describes catalytic DDQ oxidations and known CDC reactions. This is followed by our research findings with photo-activated BQH2 in Chapter Three.

The use of visible light and BQH2 is extended to the synthesis of benzylic esters in Chapter Four. The protocol employs sub-stoichiometric quantities of BQH2 and copper chloride dihydrate in dimethyl carbonate (DMC) and displays how the natural product arbutin, derived from bearberry (uva-ursi) leaves, may also be used as a sustainable pre-oxidant.

The oxidation of unactivated alkanes is discussed in Chapter Five. Discussed are Nature’s approaches, both metal and non-metal mediated to oxidise alkanes. The most common modern synthetic procedures for such transformations are also reviewed as well as previous work by the Moody Group.

Chapter Six reports the research findings which focus on the further exploration of the work published by the Moody group, focusing on the use of commercial hydrogen peroxide solutions commonly used in cleaning as an oxidant in the presence of acid. Work has been conducted to optimise existing conditions and further investigate the scope of the reaction. Potential future work in this area is also reported.

Chapter Seven contains full experimental details for the described research.

Item Type: Thesis (University of Nottingham only) (PhD)
Supervisors: Moody, Christopher
Keywords: Oxidation, Organic chemistry, C-H oxidation
Subjects: Q Science > QD Chemistry > QD241 Organic chemistry
Faculties/Schools: UK Campuses > Faculty of Science > School of Chemistry
Item ID: 56177
Depositing User: Finney, Laura
Date Deposited: 17 Jul 2019 04:40
Last Modified: 15 Nov 2023 13:24
URI: https://eprints.nottingham.ac.uk/id/eprint/56177

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