title: Transimination reactions in [b-3C-im][NTf2] ionic liquid.
abstract: Compared to conventional molecular solvents, the ionic liquid [b-3C-im][NTf(2)] was found to promote transimination reactions with up to ∼100-fold rate enhancement. This rate effect observed at ambient temperature might be explained by the fact that the ionic liquid displays weak Lewis acidity with very low, if any, nucleophilicity and its imidazolium cation is expected to interact by associating with, and thus electrophilically activating, the C=N bond of the starting imine, leading to increased stabilization of the polar, charged intermediate species and ultimately, rapid product formation. Moreover, the presence of 1 mol% Sc(OTf)(3) in [b-3C-im][NTf(2)] further facilitates the transimination reactions studied.
authors.affiliation: Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi, Taiwan, ROC.
authors.forename: Chao-Wen
authors.initials: CW
authors.lastname: Chen
authors.forename: Ming-Chung
authors.initials: MC
authors.lastname: Tseng
authors.forename: San-Kai
authors.initials: SK
authors.lastname: Hsiao
authors.forename: Wen-Hao
authors.initials: WH
authors.lastname: Chen
authors.forename: Yen-Ho
authors.initials: YH
authors.lastname: Chu
mesh_terms: D000588:Amines / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D007097:Imines / Q000138:chemical synthesis* / Q000737:chemistry*; D052578:Ionic Liquids / Q000737:chemistry*; D007700:Kinetics; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000737:chemistry*; D013696:Temperature
chemical_list: D000588:Amines; D019086:Bridged Bicyclo Compounds, Heterocyclic; D007097:Imines; D052578:Ionic Liquids; D013449:Sulfonamides