Abstract
With the ever-increasing demand for more energy and more "stuff" the majority of which is derived in some way from fossil fuels, the need to find alternative sources for energy and chemicals has never been greater. The development of a sustainable chemical industry will be reliant on the use of biomass derived products for future synthetic needs. One such compound is levoglucosenone, a pyrolytic product of cellulose that has great potential as a chiral synthon and is the focus of this project.A useful method for the microwave pyrolysis of cellulose has been developed alongside an inductively heated method with some brief explorations into the separation and quantitative analysis of the resulting bio-oils.
A novel microwave-assisted method for the synthesis of oximinoalcohols has been developed that allows deoxy-aminosugars to be synthesised from levoglucosenone in a reliable and consistent manner. A microwave-assisted Baeyer-Villiger oxidation has been developed which allows for rapid access to a range of substituted chiral butyrolactones with potential for the synthesis of substituted deoxy-nucleoside analogues.
Synthesis of C-2 aminosugars from oximes of levoglucosenone and derivatives has also been explored. Microwave-assisted epoxidations, which dramatically reduce the reaction time, have also been developed.
The conjugate addition of phosphorus nucleophiles to levoglucosenone (phospha-Michael addition) to synthesis novel chiral organophosphorus intermediates has also been briefly explored.
| Date of Award | Jul 2019 |
|---|---|
| Original language | English |
| Awarding Institution |
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| Sponsors | Northern Ireland Department for the Economy |
| Supervisor | Gary Sheldrake (Supervisor) |