Reaction of elemental chalcogens with imidazolium acetates to yield imidazole-2-chalcogenones: direct evidence for ionic liquids as proto-carbenes

被引:168
作者
Rodriguez, Hector [1 ,2 ]
Gurau, Gabriela [1 ,3 ,4 ]
Holbrey, John D. [1 ]
Rogers, Robin D. [1 ,3 ,4 ]
机构
[1] Queens Univ Belfast, Sch Chem & Chem Engn, QUILL, Belfast, Antrim, North Ireland
[2] Univ Santiago de Compostela, Dept Chem Engn, E-15782 Santiago De Compostela, Spain
[3] Univ Alabama, Dept Chem, Tuscaloosa, AL 35487 USA
[4] Univ Alabama, Ctr Green Mfg, Tuscaloosa, AL 35487 USA
关键词
SALTS; EVOLUTION; SOLVENTS; AMINES;
D O I
10.1039/c0cc05223j
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Mechanistic analysis of the reaction between elemental sulfur or selenium and 1,3-dialkylimidazolium acetate ionic liquids, in the absence of an external base or solvent, affords evidence for the equilibrium presence of carbene species in these ionic liquids. It demonstrates the potential to control, through anion selection, the concentration of carbene in stable ionic liquids.
引用
收藏
页码:3222 / 3224
页数:3
相关论文
共 32 条
[1]   An air stable carbene and mixed carbene "dimers" [J].
Arduengo, AJ ;
Davidson, F ;
Dias, HVR ;
Goerlich, JR ;
Khasnis, D ;
Marshall, WJ ;
Prakasha, TK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (52) :12742-12749
[2]  
ARDUENGO AJ, 2008, Patent No. 0171883
[3]  
ARDUENGO AJ, 1991, Patent No. 9118937
[4]  
Arduengo III A. J., 1992, [U.S. Patent, Chem. Abstr.], Patent No. [5104993, 5,104,993]
[5]  
Arduengo III A. J., 1991, U.S. Patent, Patent No. [5077414, 5,077,414]
[6]  
Benac B.L., 1986, ORG SYNTH, V64, P92
[7]   Confused ionic liquid ions-a "liquification'' and dosage strategy for pharmaceutically active salts [J].
Bica, Katharina ;
Rogers, Robin D. .
CHEMICAL COMMUNICATIONS, 2010, 46 (08) :1215-1217
[8]   On the dissolution of non-metallic solid elements (sulfur, selenium, tellurium and phosphorus) in ionic liquids [J].
Boros, Eva ;
Earle, Martyn J. ;
Gilea, Manuela A. ;
Metlen, Andreas ;
Mudring, Anja-Verena ;
Rieger, Franziska ;
Robertson, Allan J. ;
Seddon, Kenneth R. ;
Tomaszowska, Alina A. ;
Trusov, Lev ;
Vyle, Joseph S. .
CHEMICAL COMMUNICATIONS, 2010, 46 (05) :716-718
[9]  
Cetinkaya B, 1996, ARZNEIMITTEL-FORSCH, V46, P1154
[10]   Towards a Molecular Understanding of Cation-Anion Interactions-Probing the Electronic Structure of Imidazolium Ionic Liquids by NMR Spectroscopy, X-ray Photoelectron Spectroscopy and Theoretical Calculations [J].
Cremer, Till ;
Kolbeck, Claudia ;
Lovelock, Kevin R. J. ;
Paape, Natalia ;
Woelfel, Rene ;
Schulz, Peter S. ;
Wasserscheid, Peter ;
Weber, Henry ;
Thar, Jens ;
Kirchner, Barbara ;
Maier, Florian ;
Steinrueck, Hans-Peter .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (30) :9018-9033