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Synthesis of Substituted Oxabenzonorbornadienes and their Reactions

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dc.contributor.advisor Tam, William
dc.contributor.author Haner, Jamie
dc.date.accessioned 2011-09-06T15:53:37Z
dc.date.available 2011-09-06T15:53:37Z
dc.date.copyright 2011-08
dc.date.created 2011-08-29
dc.date.issued 2011-09-06
dc.identifier.uri http://hdl.handle.net/10214/2958
dc.description.abstract This thesis describes investigations on the topic of the versatile organic scaffold, 7-oxabenzonorbornadiene. The synthesis of 2-alkyl substituted furans via iron-catalyzed coupling of Grignard reagents and 2-bromofuran was optimized and various groups were coupled to furan. Primary and secondary alkyl groups were coupled with moderate to low yields of up to 56% were obtained. Furan-benzyne cycloaddition led to the formation of the corresponding C-1 substituted oxabenzonorbornadiene in yields of up to 70%. This methodology allows for access to uniquely substituted, strained bicyclic alkenes for further studies. The second part of this thesis describes the cyclopropanation of oxabenzonorbornadiene and the subsequent discovery of several reactions of the cyclopropane. The conditions for cyclopropanation were optimized, obtaining this product in yields of up to 98%. Treatment of this cyclopropane under electrophilic conditions led to the formation of (2-naphthyl)methanes in up to 98% yields, whereas treatment under nucleophilic conditions led to the formation of dihydronaphthols in up to >99% yield. The optimization of these reactions and mechanistic studies are described. en_US
dc.language.iso en en_US
dc.rights.uri http://creativecommons.org/licenses/by-nc-nd/2.5/ca/ *
dc.subject Oxabenzonorbornadiene en_US
dc.subject Cycloaddition en_US
dc.subject Organic Chemistry en_US
dc.subject Synthesis en_US
dc.title Synthesis of Substituted Oxabenzonorbornadienes and their Reactions en_US
dc.type Thesis en_US
dc.degree.programme Chemistry en_US
dc.degree.name Master of Science en_US
dc.degree.department Department of Chemistry en_US
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