Facile synthesis of aryl- and alkyl-bis(trifluoromethylsulfonyl)methanes

被引:51
作者
Hasegawa, A
Ishikawa, T
Ishihara, K
Yamamoto, H
机构
[1] Nagoya Univ, Grad Sch Engn, Nagoya, Aichi 4648603, Japan
[2] Univ Chicago, Dept Chem, Chicago, IL 60637 USA
关键词
D O I
10.1246/bcsj.78.1401
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Various arylbis(trifluoromethylsulfonyl)methanes (1) have been synthesized by reacting the corresponding benzylic halides with sodium trifluoromethanesulfinate and then with triflic anhydride. In addition, when the aryl group of 1 is a pentafluorophenyl group, the nucleophilic para-substitution of the aryl group with alkyllithiums and sodium alkoxides occurs. This reaction is useful for the design of new Bronsted acids.
引用
收藏
页码:1401 / 1410
页数:10
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共 42 条
[1]   Sterically encumbered (perfluoroaryl) borane and aluminate cocatalysts for tuning cation - Anion ion pair structure and reactivity in metallocene polymerization processes. A synthetic, structural, and polymerization study [J].
Chen, YX ;
Metz, MV ;
Li, LT ;
Stern, CL ;
Marks, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (25) :6287-6305
[2]  
Cossy J, 2002, SYNLETT, P45
[3]  
Coumont R., 1997, Synthesis, P691
[4]   A ONE-POT SYNTHESIS OF M-TERPHENYLS VIA A 2-ARYNE SEQUENCE [J].
DU, CJF ;
HART, H ;
NG, KKD .
JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (16) :3162-3165
[5]   IMPROVED SYNTHESIS OF TRIFLUOROMETHYL SULFONES USED AS INTERMEDIATES FOR THE PREPARATION OF DISUBSTITUTED OR TRI-SUBSTITUTED OLEFINS [J].
EUGENE, F ;
LANGLOIS, B ;
LAURENT, E .
JOURNAL OF FLUORINE CHEMISTRY, 1994, 66 (03) :301-309
[6]   SYNTHESIS, PROPERTIES, AND REACTIONS OF BIS((TRIFLUOROMETHYL)SULFONYL) IMIDE, (CF3SO2)2NH [J].
FOROPOULOS, J ;
DESMARTEAU, DD .
INORGANIC CHEMISTRY, 1984, 23 (23) :3720-3723
[7]   Trimethylsilyl pentafluorophenylbis(trifluoromethanesulfonyl)methide as a super Lewis acid catalyst for the condensation of trimethylhydroquinone with isophytol [J].
Hasegawa, A ;
Ishihara, K ;
Yamamoto, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (46) :5731-5733
[8]   TRIFLONES (CF3SO2C) - SURVEY OF REACTIVITY AND SYNTHETIC UTILITY [J].
HENDRICKSON, JB ;
GIGA, A ;
WAREING, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (07) :2275-2276
[9]   SYNTHETIC MANIPULATION OF TRIFLONE GROUP - FORMATION FROM ALCOHOLS, CONSTRUCTIONS, AND CONVERSION TO KETONES AND AMINES [J].
HENDRICKSON, JB ;
SKIPPER, PL .
TETRAHEDRON, 1976, 32 (14) :1627-1635
[10]   TRIFLUOROMETHANESULFONIC ACID AND DERIVATIVES [J].
HOWELLS, RD ;
MCCOWN, JD .
CHEMICAL REVIEWS, 1977, 77 (01) :69-92