The "non-nucleophilic'' anion [Tf2N]- competes with the nucleophilic Br- :: an unexpected trapping in the dediazoniation reaction in ionic liquids

被引:38
作者
Bini, R [1 ]
Chiappe, C [1 ]
Marmugi, E [1 ]
Pieraccini, D [1 ]
机构
[1] Dipartimento Chim Bioorgan & Biofarm, I-56126 Pisa, Italy
关键词
D O I
10.1039/b514988f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Imidazolium ionic liquids containing [Tf2N](-) anion are not as innocent as they are often considered; [Tf2N](-) is more reactive than Br- in heterolytic dediazoniation reactions.
引用
收藏
页码:897 / 899
页数:3
相关论文
共 19 条
[1]   The role of hydrogen bonding in controlling the selectivity of Diels-Alder reactions in room-temperature ionic liquids [J].
Aggarwal, A ;
Lancaster, NL ;
Sethi, AR ;
Welton, T .
GREEN CHEMISTRY, 2002, 4 (05) :517-520
[2]   Nucleophilic substitution of chlorobis(4-methoxyphenyl)methane: reactivity of carbenium ions in ILs-trifluoroethanol mixtures [J].
Bini, R ;
Chiappe, C ;
Pieraccini, D ;
Picc, P ;
Pomelli, CS .
TETRAHEDRON LETTERS, 2005, 46 (39) :6675-6678
[3]  
BRYSON RU, 2005, J AM CHEM SOC, V127, P2888
[4]   Ionic liquids: solvent properties and organic reactivity [J].
Chiappe, C ;
Pieraccini, D .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (04) :275-297
[5]   Kinetic study of the addition of trihalides to unsaturated compounds in ionic liquids.: Evidence of a remarkable solvent effect in the reaction of ICl2- [J].
Chiappe, C ;
Pieraccini, D .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (18) :6059-6064
[6]   Manipulating solute nucleophilicity with room temperature ionic liquids [J].
Crowhurst, L ;
Lancaster, NL ;
Arlandis, JMP ;
Welton, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (37) :11549-11555
[7]   Revisiting the reactions of nucleophiles with arenediazonium ions:: dediazoniation of arenediazonium salts in aqueous and micellar solutions containing alkyl sulfates and alkanesulfonates and an ab initio analysis of the reaction pathway [J].
Cuccovia, IM ;
da Silva, MA ;
Ferraz, HMC ;
Pliego, JR ;
Riveros, JM ;
Chaimovich, H .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2000, (09) :1896-1907
[8]   Gaseous supramolecules of imidazolium ionic liquids: "Magic" numbers and intrinsic strengths of hydrogen bonds [J].
Gozzo, FC ;
Santos, LS ;
Augusti, R ;
Consorti, CS ;
Dupont, J ;
Eberlin, MN .
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (23) :6187-6193
[9]   Fluorodediazoniation in ionic liquid solvents: new life for the Balz-Schiemann reaction [J].
Laali, KK ;
Gettwert, VJ .
JOURNAL OF FLUORINE CHEMISTRY, 2001, 107 (01) :31-34
[10]   A study of halide nucleophilicity in ionic liquids [J].
Lancaster, NL ;
Welton, T ;
Young, GB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (12) :2267-2270