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Investigations into the Palladium and Rhodium Catalyzed Ring Opening Reactions of C1-Substituted Oxabicyclic Alkenes.

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dc.contributor.advisor Tam, William
dc.contributor.author Edmunds, Michael
dc.date.accessioned 2015-01-05T19:49:06Z
dc.date.available 2015-01-05T19:49:06Z
dc.date.copyright 2014-12
dc.date.created 2014-12-09
dc.date.issued 2015-01-05
dc.identifier.uri http://hdl.handle.net/10214/8651
dc.description.abstract Optimized conditions for rhodium and palladium catalyzed ring opening reactions of C1-substituted oxabicyclic alkenes using aryl boronic acid and aryl iodide nucleophiles was developed. The effect of substitution on the aryl nucleophile as well as the effect of C1 substitution on the oxabicyclic alkenes was also studied. Nucleophiles carrying electron-donating substituents provided the ring opened products in excellent yields regardless of the position, while electron withdrawing substituents were more susceptible to steric interactions. Although two different regioisomers are possible, all reactions were found to be highly regioselective, providing single regioisomers in each case. When under palladium catalysis, ring opened products containing electron withdrawing groups rapidly underwent base catalyzed dehydration into the corresponding naphthalene derivatives. For each study a new mechanism was also proposed based on our findings. en_US
dc.description.sponsorship NSERC en_US
dc.language.iso en en_US
dc.subject Ring Opening en_US
dc.subject oxabenzonorbornadiene en_US
dc.subject oxanorbornadiene en_US
dc.subject nucleophilic en_US
dc.subject rhodium en_US
dc.subject palladium en_US
dc.subject oxabenzonorbornadiene en_US
dc.subject bicyclic en_US
dc.subject alkene en_US
dc.subject metal en_US
dc.subject catalyst en_US
dc.subject naphthol en_US
dc.subject naphthalene en_US
dc.subject substituted en_US
dc.subject unsymmetrical en_US
dc.title Investigations into the Palladium and Rhodium Catalyzed Ring Opening Reactions of C1-Substituted Oxabicyclic Alkenes. en_US
dc.type Article 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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