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Synthesis and reactivity of α-diazosulfoxides and α-diazosulfones
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Date
2024
Authors
Ní Thuama, Eilís
Journal Title
Journal ISSN
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Publisher
University College Cork
Published Version
Abstract
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.
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Keywords
Diazosulfoxides , Diazosulfones , Flow chemistry , Continuous processing
Citation
Ní Thuama, E. 2024. Synthesis and reactivity of α-diazosulfoxides and α-diazosulfones. MRes Thesis, University College Cork.