Organocuprate reactions in phosphonium-based ionic liquids

Show simple item record

dc.contributor.advisor Singer, Robert D. (Robert Douglas), 1964-
dc.creator Kyle, Christian Boyd 2011-05-12T13:06:50Z 2011-05-12T13:06:50Z 2009
dc.identifier.other QD189 K95 2009
dc.description xiii, 91 leaves : ill. ; 29 cm. en_CA
dc.description Includes abstract.
dc.description Includes bibliographical references (leaves 88-91).
dc.description.abstract Ionic liquids (ILs) based on the trihexyl(tetradecyl)phosphonium cation were purified or synthesized in high yields (83.6-93.0 %) via salt metathesis. These were used as solvents for 1,4-congugate additions of lithium dibutylcyanocuprate [Bu₂CuLi∙LiCN] to trans -aphenyl-3-buten-2-one; with and without tetrahydofuran co-solvent. Low conversion of substrate to product (4-phenyloctane-2-one) was achieved in 1 hour (0-59 %) in the IL alone while retaining the organic solvent offers better product formation (65-94 %) as determined by GC-MS analysis. Good stability of the cuprate in the ILs is experienced when the chloride anion is exchanged for bis(trifluoromethylsulfonyl)amide or dicyanimide, greatly reducing undesired alkenes formed via in situ generation of Wittig reagents from the cation. Methods to isolate the product and recycle the IL after reaction require further work. Three ether containing ILs were also synthesized in good yields (66.8-75.9 %); however, their hygroscopic nature proved deleterious to their role in the model reaction. en_CA
dc.description.provenance Submitted by Mollie Thompson ( on 2011-05-12T13:06:50Z No. of bitstreams: 0 en
dc.description.provenance Made available in DSpace on 2011-05-12T13:06:50Z (GMT). No. of bitstreams: 0 Previous issue date: 2009 en
dc.language.iso en en_CA
dc.publisher Halifax, N.S. : Saint Mary's University en_CA
dc.subject.lcc QD189
dc.subject.lcsh Ionic solutions
dc.subject.lcsh Organophosphorus compounds
dc.subject.lcsh Organocopper compounds
dc.subject.lcsh Solvents -- Environmental aspects
dc.title Organocuprate reactions in phosphonium-based ionic liquids en_CA
dc.type Text en_CA Master of Science in Applied Science Masters Chemistry Saint Mary's University (Halifax, N.S.)
 Find Full text

Files in this item


This item appears in the following Collection(s)

Show simple item record

Search DSpace


My Account