Investigation on Novel Reactions of Oxabenzonorbornadienes and Cyclopropanated Oxabenzonorbornadienes

dc.contributor.advisorTam, William
dc.contributor.authorHo, Angel
dc.date.accessioned2020-04-20T18:08:50Z
dc.date.copyright2020-04
dc.date.created2020-04-07
dc.date.issued2020-04-20
dc.degree.departmentDepartment of Chemistryen_US
dc.degree.grantorUniversity of Guelphen_US
dc.degree.nameMaster of Scienceen_US
dc.degree.programmeChemistryen_US
dc.description.abstractThe present work demonstrates the first examples of carboxylic acid-tethered cyclopropanated oxabenzonorbornadienes (CPOBDs) to undergo ring-opening reactions in mild acidic conditions. Two regioisomers are formed but the reactions are highly regioselective towards type 3 ring-opened products. It was observed that substitution at the C-5 and aryl positions of CPOBD significantly hinders the ring-opening reactions leading to poor yields of ring-opened product, although high regioselectivity for the type 3 ring-opened product is still maintained. The second part of this thesis outlines a study on the regio- and stereo-chemistry of the iridium-catalyzed hydroacylation of C1-substituted OBDs with salicylaldehyde. The scope of the reaction was expanded to include various electron-donating, electron-withdrawing and bulky substituents to investigate the electronic and steric effects of the C1- substituent on the hydroacylation reaction. It was observed that the addition occurred exclusively at the less hindered, C3 position to give the corresponding adducts.en_US
dc.description.embargo2021-04-07
dc.identifier.urihttp://hdl.handle.net/10214/17865
dc.language.isoenen_US
dc.publisherUniversity of Guelphen_US
dc.rightsAttribution-NoDerivatives 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nd/4.0/*
dc.subjectoxabenzonorbornadienesen_US
dc.subjectring-opening reactionsen_US
dc.subjecthydroacylationen_US
dc.subjectacid-catalyzeden_US
dc.subjectIridium-catalyzeden_US
dc.subjectcyclopropanated oxabenzonorbornadienesen_US
dc.titleInvestigation on Novel Reactions of Oxabenzonorbornadienes and Cyclopropanated Oxabenzonorbornadienesen_US
dc.typeThesisen_US

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