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oai:cora.ucc.ie:10468/169992025-02-07T02:03:35Zcom_10468_178com_10468_5com_10468_388com_10468_1col_10468_10433col_10468_9859col_10468_8983

2035-05-31 Maguire, Anita Collins, Stuart Ní Thuama, Eilís 2025-02-06T14:53:55Z 2025-02-06T14:53:55Z 2024 2024 The focus of this body of work has been the synthesis of stable mono and bicyclic α-diazosulfoxides and their subsequent reactivity. A range of α-diazosulfoxides have been synthesised by the Maguire-Collins research group since the mid-1990s using a Regitz diazo transfer method. In this work in situ NMR monitoring has been used to gain a deeper understanding of the relative reactivity of diastereomeric sulfoxides in this reaction. α-Diazosulfoxides were synthesised using flow and batch reaction conditions. Continuous flow processing enabled the α-diazosulfoxide synthesis using an in situ generated sulfonyl azide for the first time, resulting in a greater safety profile for the process. Investigations into the synthesis of related mono and bicyclic α-diazosulfones were also undertaken, in both batch and flow. The α-diazosulfoxides are known to react via a hetero-Wolff rearrangement to form α-oxo sulfines. The 1,3-dipolar cycloadditions of these α-oxo sulfines were investigated further under Rh catalysis and a study into the photoreactivity of the α-diazosulfoxides on flow was also performed. Not peer reviewed Accepted Version application/pdf Ní Thuama, E. 2024. Synthesis and reactivity of α-diazosulfoxides and α-diazosulfones. MRes Thesis, University College Cork. 112 https://hdl.handle.net/10468/16999 en University College Cork © 2024, Eilís Ní Thuama. https://creativecommons.org/licenses/by/4.0/ Diazosulfoxides Diazosulfones Flow chemistry Continuous processing Synthesis and reactivity of α-diazosulfoxides and α-diazosulfones Masters thesis (Research) Masters MRes - Master of Researchinfo:eu-repo/semantics/embargoedAccess