Electrophilic catalysis in nucleophilic substitution reactions in ionic liquids

被引:4
作者
Cavazza, M [1 ]
Pietra, F [1 ]
机构
[1] Univ Pisa, Dipartimento Chim & Chim Ind, I-56100 Pisa, Italy
关键词
D O I
10.1016/j.tetlet.2004.03.050
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-Chlorotropone was obtained from 2-tosyloxytropone in 88% yield in the recyclable ionic medium BMIMBF4/LiCl. That Li+ acts as a Lewis acid was proven by the lack of reactivity of 2-tosyloxytropone, under the above conditions, on replacing LiCl with NaCl or BMIMCl, or using BMIMCl alone, or a BMIMBF4/MeCN/KCl mixture. 2-Bromo- and 2-iodotropone were obtained along similar lines from LiBr or LiI, respectively, whereas LiF proved unreactive. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3633 / 3634
页数:2
相关论文
共 12 条
[1]   A general entry to 10-halocolchicides and 9-haloisocolchicides [J].
Cavazza, M ;
Pietra, F .
SYNTHETIC COMMUNICATIONS, 1997, 27 (19) :3405-3413
[2]   REACTIONS OF HALOTROPONES AND RELATED COMPOUNDS [J].
DOERING, WV ;
HISKEY, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (22) :5688-5693
[3]   REARRANGEMENT OF HALOTROPONES - CHLORIDE EXCHANGE IN TRIBROMOTROPOLONE [J].
DOERING, WV ;
KNOX, LH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1952, 74 (22) :5683-5687
[4]   Polymer-supported ionic liquids: Imidazolium salts as catalysts for nucleophilic substitution reactions including fluorinations [J].
Kim, DW ;
Chi, DY .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (04) :483-485
[5]   Significantly enhanced reactivities of the nucleophilic substitution reactions in ionic liquid [J].
Kim, DW ;
Song, CE ;
Chi, DY .
JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (11) :4281-4285
[6]   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
[7]   Nucleophilicity in ionic liquids. 2. Cation effects on halide nucleophilicity in a series of bis(trifluoromethylsulfonyl)imide ionic liquids [J].
Lancaster, NL ;
Salter, PA ;
Welton, T ;
Young, GB .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (25) :8855-8861
[8]   REACTIVITY OF PSEUDOAROMATIC COMPOUNDS .4. NORMAL SUBSTITUTIONS OF 2-SUBSTITUTED TROPONES BY SECONDARY OR TERTIARY AMINES - ABNORMAL BEHAVIOUR OF 2-FLUOROTROPONE [J].
PIETRA, F ;
DELCIMA, F .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1971, (11) :2224-&
[9]  
ROGERS RD, 2003, NATO SCI SERIES, V92
[10]  
Wasserscheid P, 2000, ANGEW CHEM INT EDIT, V39, P3772, DOI 10.1002/1521-3773(20001103)39:21<3772::AID-ANIE3772>3.0.CO