Bis-thiourea based ionic organocatalysts

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dc.contributor.advisor Singer, Robert D. (Robert Douglas), 1964-
dc.creator Watson, Andrew Allison
dc.date.accessioned 2015-04-27T13:55:39Z
dc.date.available 2015-04-27T13:55:39Z
dc.date.issued 2015
dc.identifier.uri http://library2.smu.ca/xmlui/handle/01/26077
dc.description 1 online resource (vii, 52 p.) : ill. (some col.)
dc.description Includes abstract.
dc.description Includes bibliographical references (p. 50-52).
dc.description.abstract Ionic liquids and organocatalysts serve as greener alternatives to conventional reaction solvents and catalysts. Recent research has found that pyrrolidinium tagged ionic organocatalysts enhance the rate of DABCO co-catalyzed Morita-Baylis-Hillman reactions and remain entrained in ionic liquid media. Three bis-thiourea based ionic organocatalysts have been synthesized. 1,1-bis(4-(3-(3,5-bis(trifluoromethyl)phenyl)thioureido)benzyl)pyrrolidinium hexafluorophosphate(V) was successfully employed in the DABCO co-catalyzed rate enhancement of the reaction between benzaldehyde and cyclohex-2-en-1-one. 95 % conversion to product was attained at 5 mol% catalyst loading. This room-temperature reaction used the ionic liquid N-butyl-N-methylpyrrolidiniumbis(trifluoromethane)sulfonamide, [BMPyr][N(Tf)[subscript 2]], as the reaction solvent. Attempts at recycling the catalyst resulted in low conversion with no evidence of catalyst leaching. Microwave irradiation of the MBH reactions was attempted, with low conversion to product attributed to thermal degradation of the catalyst. en_CA
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dc.description.provenance Made available in DSpace on 2015-04-27T13:55:39Z (GMT). No. of bitstreams: 1 Watson_Andrew_Honours_2015.pdf: 1296205 bytes, checksum: 20b6e3a5034739c21e5f39f1ec175382 (MD5) Previous issue date: 2015-04-24 en
dc.language.iso en en_CA
dc.publisher Halifax, N.S. : Saint Mary's University
dc.title Bis-thiourea based ionic organocatalysts 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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