{"id":{"repo_id":"houston","oai_identifier":"oai:uh-ir.tdl.org:10657/5552"},"canonical_url":"https://search.dev.ndltd.org/etd/houston/oai:uh-ir.tdl.org:10657/5552","repository":{"repo_id":"houston","name":"University of Houston","base_url":"https://uh-ir.tdl.org/server/oai/request"},"display":{"title":"Benign Catalysis and Expansion of Cyclobenzoins","abstract":"Cyclobenzoins are a fledgling class of macrocycles first reported by the Miljanić group in 2015. Since the first reports, several modifications to the original two compounds, cyclotribenzoin and cyclotetrabenzoin, have been reported, but no developments on the production have been reported. Whether this is due to the use of sodium cyanide as a catalyst or the small substrate scope, this thesis aims to improve on both limitations. The first issue, the cyanide catalyst, presented an opportunity to develop a new method to synthesize cyclotetrabenzoin. After testing a series of N-heterocyclic carbene catalysts, a suitable alternative was determined. Initial results indicated a substantial drop in yield, but optimizing conditions brought the production from the N-heterocyclic carbene conditions into line with the cyanide-catalyzed conditions. Concerning the substrate scope, initial experiments suggested that the general poor solubility of the aromatic dialdehyde materials in the aqueous conditions prevented their use as cyclobenzoin precursors. Leveraging the newly developed N-heterocyclic carbenes, particularly the ability to utilize organic solvents, two completely novel cyclobenzoins were prepared and characterized.","abstract_html":"Cyclobenzoins are a fledgling class of macrocycles first reported by the Miljanić group in 2015. Since the first reports, several modifications to the original two compounds, cyclotribenzoin and cyclotetrabenzoin, have been reported, but no developments on the production have been reported. Whether this is due to the use of sodium cyanide as a catalyst or the small substrate scope, this thesis aims to improve on both limitations. The first issue, the cyanide catalyst, presented an opportunity to develop a new method to synthesize cyclotetrabenzoin. After testing a series of N-heterocyclic carbene catalysts, a suitable alternative was determined. Initial results indicated a substantial drop in yield, but optimizing conditions brought the production from the N-heterocyclic carbene conditions into line with the cyanide-catalyzed conditions. Concerning the substrate scope, initial experiments suggested that the general poor solubility of the aromatic dialdehyde materials in the aqueous conditions prevented their use as cyclobenzoin precursors. Leveraging the newly developed N-heterocyclic carbenes, particularly the ability to utilize organic solvents, two completely novel cyclobenzoins were prepared and characterized.","abstract_has_math":false,"creators":["Eisterhold, Andrew Michael 1990-"],"institution":"University of Houston","degree_name":"Master of Science","degree_level":"Masters","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":["Miljanić, Ognjen Š."],"committee_chairs":[],"committee_members":["Daugulis, Olafs","Harth, Eva M.","Jacobson, Allan J.","Krishnamoorti, Ramanan"],"year":2019,"date_issued":"2019-12","date_published":"2019-12","updated_at":"2026-07-24T02:32:34Z","subjects":["Cyclobenzoin","Macrocycle","Benzoin Condensation"],"languages":["eng"],"rights":["The author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s)."],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/10657/5552","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Miljanić, Ognjen Š."]},{"key":"dc:contributor.committeemember","label":"Committee Member","values":["Daugulis, Olafs","Harth, Eva M.","Jacobson, Allan J.","Krishnamoorti, Ramanan"]},{"key":"dc:creator","label":"Author","values":["Eisterhold, Andrew Michael 1990-"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2019-12-17T03:29:18Z"]},{"key":"dc:date.issued","label":"Date","values":["2019-12"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Masters"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Houston"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Cyclobenzoin","Macrocycle","Benzoin Condensation"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["eng"]},{"key":"dc:rights","label":"Dc Rights","values":["The author of this work is the copyright owner. UH Libraries and the Texas Digital Library have their permission to store and provide access to this work. Further transmission, reproduction, or presentation of this work is prohibited except with permission of the author(s)."]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.uri","label":"Identifier URI","values":["https://hdl.handle.net/10657/5552"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["Cyclobenzoins are a fledgling class of macrocycles first reported by the Miljanić group in 2015. Since the first reports, several modifications to the original two compounds, cyclotribenzoin and cyclotetrabenzoin, have been reported, but no developments on the production have been reported. Whether this is due to the use of sodium cyanide as a catalyst or the small substrate scope, this thesis aims to improve on both limitations. The first issue, the cyanide catalyst, presented an opportunity to develop a new method to synthesize cyclotetrabenzoin. After testing a series of N-heterocyclic carbene catalysts, a suitable alternative was determined. Initial results indicated a substantial drop in yield, but optimizing conditions brought the production from the N-heterocyclic carbene conditions into line with the cyanide-catalyzed conditions. Concerning the substrate scope, initial experiments suggested that the general poor solubility of the aromatic dialdehyde materials in the aqueous conditions prevented their use as cyclobenzoin precursors. Leveraging the newly developed N-heterocyclic carbenes, particularly the ability to utilize organic solvents, two completely novel cyclobenzoins were prepared and characterized."]},{"key":"dc:format.mimetype","label":"Dc Format Mimetype","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Benign Catalysis and Expansion of Cyclobenzoins"]}]}],"canonical_facts":{"dc:contributor.advisor":["Miljanić, Ognjen Š."],"dc:contributor.committeemember":["Daugulis, Olafs","Harth, Eva M.","Jacobson, Allan J.","Krishnamoorti, Ramanan"],"dc:creator":["Eisterhold, Andrew Michael 1990-"],"dc:date.accessioned":["2019-12-17T03:29:18Z"],"dc:date.issued":["2019-12"],"dc:description.abstract":["Cyclobenzoins are a fledgling class of macrocycles first reported by the Miljanić group in 2015. Since the first reports, several modifications to the original two compounds, cyclotribenzoin and cyclotetrabenzoin, have been reported, but no developments on the production have been reported. Whether this is due to the use of sodium cyanide as a catalyst or the small substrate scope, this thesis aims to improve on both limitations. The first issue, the cyanide catalyst, presented an opportunity to develop a new method to synthesize cyclotetrabenzoin. After testing a series of N-heterocyclic carbene catalysts, a suitable alternative was determined. Initial results indicated a substantial drop in yield, but optimizing conditions brought the production from the N-heterocyclic carbene conditions into line with the cyanide-catalyzed conditions. Concerning the substrate scope, initial experiments suggested that the general poor solubility of the aromatic dialdehyde materials in the aqueous conditions prevented their use as cyclobenzoin precursors. 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