Restriction lift date: 2035-05-31
Photochemical transformations of α-diazocarbonyl compounds in flow
Loading...
Files
Date
2024
Authors
O'Callaghan, Katie S.
Journal Title
Journal ISSN
Volume Title
Publisher
University College Cork
Published Version
Abstract
This thesis describes a detailed investigation of the synthetic and mechanistic aspects of the reactivity of a series of α-diazocarbonyl compounds including aryldiazoacetates, α-diazo-β-ketoesters and an α-diazo-β-ketosulfone, under continuous flow photolysis. These photochemical transformations yielded 2,3-dihydrobenzofurans, γ- and β-lactones, oxazoles and Wolff rearrangement products indicating the synthetic versatility of these metal-free processes. Continuous flow technology was also applied to telescope sulfonyl azide generation, diazo transfer and subsequent photochemical reactions, enabling three steps to be carried out without the need to isolate or handle any hazardous materials. The use of Process Analytical Technologies (FlowNMR and FlowIR™) throughout this work provided key insights into reaction progress and offered improved process safety through reaction monitoring.
Description
Keywords
α-Diazocarbonyl compounds , Photochemistry , Flow chemistry
Citation
O'Callaghan, K. S. 2024. Photochemical transformations of α-diazocarbonyl compounds in flow. PhD Thesis, University College Cork.