Phosphonium ionic liquid based salen ligands for use in catalysis

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dc.contributor.advisor Singer, Robert D. (Robert Douglas), 1964-
dc.creator Prudhoe, Christine
dc.date.accessioned 2013-05-02T17:41:30Z
dc.date.available 2013-05-02T17:41:30Z
dc.date.issued 2013
dc.identifier.uri http://library2.smu.ca/xmlui/handle/01/24911
dc.description 1 online resource (viii, 70 p.) : ill.
dc.description Includes abstract and appendix.
dc.description Includes bibliographical references (p. 57-61).
dc.description.abstract Salen ligands and their corresponding complexes are well known in the field of asymmetric catalysis due to their success in stereoselective reactions. A method that easily allows for recycling of the catalyst without degradation of catalytic activity would make them more industrially viable. The generation of a Task Specific Ionic Liquid (TSIL) by attaching tributylphosphonium moieties to Jacobsen’s ligand could promote the entrainment of the catalyst in an ionic liquid (IL). This would potentially create a recyclable system where the desired product can be extracted, leaving the IL/catalyst layer behind ready for reuse. The racemic and asymmetric versions of the ligand, 5,5'-(1E,1'E)-(cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene))bis(methan-1-yl-1-ylidene)bis(3-tert-butyl-4-hydroxy-5,1-phenylene)bis(methylene)bis(tributylphosphonium) hexafluoridophosphate, as well as their respective copper complexes were successfully synthesized and characterized. These were applied to aziridinations of styrene, using tosyliminophenyliodinane (PhINTs) as a nitrene source, in both acetonitrile and three different ILs. Acetonitrile generated yields of up to 88%, however no product was extracted from 1-butyl-3-methylimidazolium hexafluoridophosphate, tetradecyl(trihexyl) phosphonium hexafluoridophosphate and chloride. en_CA
dc.description.provenance Submitted by Trish Grelot (trish.grelot@smu.ca) on 2013-05-02T17:41:30Z No. of bitstreams: 1 prudhoe_christine_honours_2013.pdf: 1134394 bytes, checksum: 4e0344cca2b6acd603e9adcb889ec904 (MD5) en
dc.description.provenance Made available in DSpace on 2013-05-02T17:41:30Z (GMT). No. of bitstreams: 1 prudhoe_christine_honours_2013.pdf: 1134394 bytes, checksum: 4e0344cca2b6acd603e9adcb889ec904 (MD5) en
dc.language.iso en en_CA
dc.publisher Halifax, N.S. : Saint Mary's University
dc.title Phosphonium ionic liquid based salen ligands for use in catalysis 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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