{"id":{"repo_id":"cork","oai_identifier":"oai:cora.ucc.ie:10468/16999"},"canonical_url":"https://search.dev.ndltd.org/etd/cork/oai:cora.ucc.ie:10468/16999","repository":{"repo_id":"cork","name":"University College Cork","base_url":"https://cora.ucc.ie/server/oai/request"},"display":{"title":"Synthesis and reactivity of α-diazosulfoxides and α-diazosulfones","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.","abstract_html":"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.","abstract_has_math":false,"creators":["Ní Thuama, Eilís"],"institution":"University College Cork","degree_name":null,"degree_level":null,"degree_discipline":null,"degree_department":null,"school":null,"contributors":[],"advisors":["Maguire, Anita","Collins, Stuart"],"committee_chairs":[],"committee_members":[],"year":2024,"date_issued":"2024","date_published":"2024","updated_at":"2026-07-24T01:46:44Z","subjects":["Diazosulfoxides","Diazosulfones","Flow chemistry","Continuous processing"],"languages":["en"],"rights":["© 2024, Eilís Ní Thuama."],"rights_urls":["https://creativecommons.org/licenses/by/4.0/"],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/10468/16999","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Maguire, Anita","Collins, Stuart"]},{"key":"dc:creator","label":"Author","values":["Ní Thuama, Eilís"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2025-02-06T14:53:55Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2025-02-06T14:53:55Z"]},{"key":"dc:date.issued","label":"Date","values":["2024"]},{"key":"dc:publisher","label":"Institution","values":["University College Cork"]},{"key":"dc:type","label":"Dc Type","values":["Masters thesis (Research)"]},{"key":"dc:type.qualificationlevel","label":"Dc Type Qualificationlevel","values":["Masters"]},{"key":"dc:type.qualificationname","label":"Dc Type Qualificationname","values":["MRes - Master of Research"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Diazosulfoxides","Diazosulfones","Flow chemistry","Continuous processing"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["en"]},{"key":"dc:rights","label":"Dc Rights","values":["© 2024, Eilís Ní Thuama."]},{"key":"dc:rights.uri","label":"Rights URI","values":["https://creativecommons.org/licenses/by/4.0/"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://hdl.handle.net/10468/16999"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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."]},{"key":"dc:format.mimetype","label":"Dc Format Mimetype","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Synthesis and reactivity of α-diazosulfoxides and α-diazosulfones"]}]}],"canonical_facts":{"dc:contributor.advisor":["Maguire, Anita","Collins, Stuart"],"dc:creator":["Ní Thuama, Eilís"],"dc:date.accessioned":["2025-02-06T14:53:55Z"],"dc:date.available":["2025-02-06T14:53:55Z"],"dc:date.issued":["2024"],"dc:description.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."],"dc:format.mimetype":["application/pdf"],"dc:identifier.uri":["https://hdl.handle.net/10468/16999"],"dc:language.iso":["en"],"dc:publisher":["University College Cork"],"dc:rights":["© 2024, Eilís Ní Thuama."],"dc:rights.uri":["https://creativecommons.org/licenses/by/4.0/"],"dc:subject":["Diazosulfoxides","Diazosulfones","Flow chemistry","Continuous processing"],"dc:title":["Synthesis and reactivity of α-diazosulfoxides and α-diazosulfones"],"dc:type":["Masters thesis (Research)"],"dc:type.qualificationlevel":["Masters"],"dc:type.qualificationname":["MRes - Master of Research"]},"updated_at":"2026-07-24T01:46:44Z"}