An investigation of the mechanism of the rhodium-catalyzed [5 + 1 + 2 + 1] cycloaddition reaction of vinylcyclopropanes, terminal alkynes and carbon-monoxide

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dc.contributor.advisor Ylijoki, Kai, 1978-
dc.creator Mbaezue, Ifenna
dc.date.accessioned 2017-06-02T14:44:10Z
dc.date.available 2017-06-02T14:44:10Z
dc.date.issued 2017
dc.identifier.uri http://library2.smu.ca/handle/01/27005
dc.description 1 online resource (x, 73 p.) : col. ill.
dc.description Includes abstract and appendix.
dc.description Includes bibliographical references (p. 66-69).
dc.description.abstract Spectroscopic investigations on the [RhCl(CO)[subscript 2]][subscript 2] catalysed [5 + 1 + 2 + 1] cycloaddition of VCP, CO and 4-ethynylbiphenyl were performed and the existence of an off-cycle species was revealed. This species that forms at high Rh-catalyst loading mitigates cycloadduct formation even at elevated temperatures and long reaction periods. Furthermore, the mechanism for the conversion of the inactive species to an active species was hypothesised, as informed by previous computational studies. The starting material for the spectroscopic study, VCP, was synthesised by a modified procedure. The reaction of 2-methoxyethanol with 1,3-butadiene in toluene was followed by the isolation of the resulting brominated intermediate. Subsequently, purification of the intermediate, followed by an elimination reaction afforded 2-(2-methoxyethoxy)-1,3-butadiene. A modified vacuum distillation method was used to purify the diene and subsequently, TLC monitored Simmons-Smith cyclopropanation was performed on the diene. The resulting VCP was also purified by the same method employed for the diene. en_CA
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dc.language.iso en en_CA
dc.publisher Halifax, N.S. : Saint Mary's University
dc.title An investigation of the mechanism of the rhodium-catalyzed [5 + 1 + 2 + 1] cycloaddition reaction of vinylcyclopropanes, terminal alkynes and carbon-monoxide en_CA
dc.type Text en_CA
thesis.degree.name Bachelor of Science (Honours Chemistry)
thesis.degree.level Undergraduate
thesis.degree.discipline Chemistry
thesis.degree.grantor Saint Mary's University (Halifax, N.S.)
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