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Investigation on Novel Reactions of Oxabenzonorbornadienes and Cyclopropanated Oxabenzonorbornadienes

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dc.contributor.advisor Tam, William Ho, Angel 2020-04-20T18:08:50Z 2020-04 2020-04-07 2020-04-20
dc.description.abstract The 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.language.iso en en_US
dc.rights Attribution-NoDerivatives 4.0 International *
dc.rights.uri *
dc.subject oxabenzonorbornadienes en_US
dc.subject ring-opening reactions en_US
dc.subject hydroacylation en_US
dc.subject acid-catalyzed en_US
dc.subject Iridium-catalyzed en_US
dc.subject cyclopropanated oxabenzonorbornadienes en_US
dc.title Investigation on Novel Reactions of Oxabenzonorbornadienes and Cyclopropanated Oxabenzonorbornadienes en_US
dc.type Thesis en_US Chemistry en_US Master of Science en_US Department of Chemistry en_US
dc.description.embargo 2021-04-07
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Attribution-NoDerivatives 4.0 International Except where otherwise noted, this item's license is described as Attribution-NoDerivatives 4.0 International