Synthesis and reactivity of α-diazosulfoxides and α-diazosulfones

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dc.check.date2035-05-31
dc.contributor.advisorMaguire, Anita
dc.contributor.advisorCollins, Stuart
dc.contributor.authorNí Thuama, Eilís
dc.date.accessioned2025-02-06T14:53:55Z
dc.date.available2025-02-06T14:53:55Z
dc.date.issued2024
dc.date.submitted2024
dc.description.abstractThe 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.en
dc.description.statusNot peer revieweden
dc.description.versionAccepted Versionen
dc.format.mimetypeapplication/pdfen
dc.identifier.citationNí Thuama, E. 2024. Synthesis and reactivity of α-diazosulfoxides and α-diazosulfones. MRes Thesis, University College Cork.
dc.identifier.endpage112
dc.identifier.urihttps://hdl.handle.net/10468/16999
dc.language.isoen
dc.publisherUniversity College Corken
dc.rights© 2024, Eilís Ní Thuama.
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.subjectDiazosulfoxidesen
dc.subjectDiazosulfonesen
dc.subjectFlow chemistryen
dc.subjectContinuous processingen
dc.titleSynthesis and reactivity of α-diazosulfoxides and α-diazosulfones
dc.typeMasters thesis (Research)en
dc.type.qualificationlevelMasters
dc.type.qualificationnameMRes - Master of Research
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