2026-09-24T07:17:03Zhttps://cora.ucc.ie/server/oai/request

oai:cora.ucc.ie:10468/170002025-02-07T02:04:09Zcom_10468_289com_10468_6com_10468_178com_10468_5com_10468_388com_10468_1col_10468_290col_10468_179col_10468_389col_10468_8983

2035-05-31 Maguire, Anita Collins, Stuart O'Callaghan, Katie S. Synthesis and Solid State Pharmaceutical Centre 2025-02-06T15:03:19Z 2025-02-06T15:03:19Z 2024 2024 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. Not peer reviewed Accepted Version application/pdf O'Callaghan, K. S. 2024. Photochemical transformations of α-diazocarbonyl compounds in flow. PhD Thesis, University College Cork. 465 https://hdl.handle.net/10468/17000 en University College Cork info:eu-repo/grantAgreement/SFI/SFI Research Centres/12/RC/2275/IE/Synthesis and Solid State Pharmaceutical Centre (SSPC)/ © 2024, Katie O'Callaghan. https://creativecommons.org/licenses/by/4.0/ α-Diazocarbonyl compounds Photochemistry Flow chemistry Photochemical transformations of α-diazocarbonyl compounds in flow Doctoral thesis Doctoral PhD - Doctor of Philosophyinfo:eu-repo/semantics/embargoedAccess