Ruthenium-Catalyzed [2+2] Cycloaddition Reactions between a 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene and Unsymmetrical Alkynes

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Ruthenium-Catalyzed [2+2] Cycloaddition Reactions between a 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene and Unsymmetrical Alkynes

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dc.contributor.advisor Tam, William
dc.contributor.author Durham, Robin
dc.date 2011-08-05
dc.date.accessioned 2011-08-12T12:52:09Z
dc.date.available 2011-08-12T12:52:09Z
dc.date.issued 2011-08-12
dc.identifier.uri http://hdl.handle.net/10214/2837
dc.description.abstract This thesis is an investigation of ruthenium-catalyzed [2+2] cycloaddition reactions of a 3-aza-2-oxabicyclo[2.2.1]hept-5-ene with unsymmetrical alkynes. Yields of up to 90% were obtained though regioselectivity was modest. Select cycloadducts could be separated and used to access a highly functionalized [3.2.0] bicyclic structure through reductive cleavage of the N-O bond. These ring-opened products displayed a chemical exchange phenomenon in 1D carbon NMR and required characterization by 2D NMR techniques. In addition, a haloalkynylation reaction was found to occur when 1-iodo-2-phenylethyne and the 3-aza-2-oxabicyclo[2.2.1]hept-5-ene were submitted to the cycloaddition conditions. An effort was made to optimize the reaction between 1-iodo-2-phenylethyne and norbornadiene in favour of the addition product. en_US
dc.description.sponsorship Government of Ontario, NSERC en_US
dc.language.iso en en_US
dc.subject cycloaddition en_US
dc.subject 3-aza-2-oxabicyclo[2.2.1]hept-5-ene en_US
dc.subject Ruthenium en_US
dc.subject [2+2] en_US
dc.subject ring opening en_US
dc.title Ruthenium-Catalyzed [2+2] Cycloaddition Reactions between a 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene and Unsymmetrical Alkynes 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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