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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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Title: Ruthenium-Catalyzed [2+2] Cycloaddition Reactions between a 3-Aza-2-oxabicyclo[2.2.1]hept-5-ene and Unsymmetrical Alkynes
Author: Durham, Robin
Department: Department of Chemistry
Program: Chemistry
Advisor: Tam, William
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.
URI: http://hdl.handle.net/10214/2837
Date: 2011-08
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