Intramolecular and Intermolecular Cyclizations of Benzyl Alkynyl Sulfones: Synthetic scope, Limitations and Mechanistic Studies

dc.contributor.advisorSchwan, Adrian
dc.contributor.authorHo, Uyen
dc.date.accessioned2014-05-26T19:56:10Z
dc.date.available2014-05-26T19:56:10Z
dc.date.copyright2014-05
dc.date.created2014-05-22
dc.date.issued2014-05-26
dc.degree.departmentDepartment of Chemistryen_US
dc.degree.grantorUniversity of Guelphen_US
dc.degree.nameMaster of Scienceen_US
dc.degree.programmeChemistryen_US
dc.description.abstractThis thesis encompasses the investigation of two modes of base-induced cyclizations of benzyl alkynyl sulfones. Based on works previously published by the Schwan group, the key step of the cyclization was identified to be the formation of a benzylic anion, which undergoes cyclization by temporarily breaking aromaticity. Building on the proposed theory, substrates were developed to directly probe the key step. Unfortunately, no conclusive results were obtained. However, during the study, an unexpected compound, oxathiin-S,S-dioxide was isolated. These compounds possess a heterocyclic core and belong to a family of fungicides. This discovery inspired a novel systematic approach to substrates with multiple aryl substituents. Based on retrosynthetic analysis, substrates were treated with base, followed by a benzaldehyde to effect electrophilic capture and subsequent intramolecular conjugate addition to the triple bond. After thorough optimization, the reaction affords products with (het)aryl groups at the 5- and 6-positions in 23 – 78% yield.en_US
dc.identifier.urihttp://hdl.handle.net/10214/8146
dc.language.isoenen_US
dc.publisherUniversity of Guelphen_US
dc.rights.licenseAll items in the Atrium are protected by copyright with all rights reserved unless otherwise indicated.
dc.subjectsulfoneen_US
dc.subjectcyclizationen_US
dc.titleIntramolecular and Intermolecular Cyclizations of Benzyl Alkynyl Sulfones: Synthetic scope, Limitations and Mechanistic Studiesen_US
dc.typeThesisen_US

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