HIGHLY FLUORINATED FULLERENES AS OXIDIZERS AND FLUORINATING AGENTS

被引:32
作者
GAKH, AA
TUINMAN, AA
ADCOCK, JL
COMPTON, RN
机构
[1] UNIV TENNESSEE,DEPT CHEM,KNOXVILLE,TN 37996
[2] OAK RIDGE NATL LAB,OAK RIDGE,TN 37831
关键词
D O I
10.1016/S0040-4039(00)79278-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Contrary to the chemistry of ''standard'' fluorocarbons, highly fluorinated fullerenes (C60F44 - C60F46) display distinct oxidizing and fluorinating properties. They liberate iodine from NaI solutions, oxidize isopropanol to acetone, and fluorinate aromatic compounds in the presence of acid catalysts such as BF3.Et2O. Fluoroaromatic products are also generated in the reaction of these fluorofullerenes with organolithium reagents. Even the relatively unreactive heterocycle pyridine is fluorinated by the higher fluorofullerenes. Reaction mechanisms are proposed to explain these observations.
引用
收藏
页码:7167 / 7170
页数:4
相关论文
共 14 条
[1]   NUCLEOPHILIC-SUBSTITUTION VERSUS ELECTRON-TRANSFER .1. ON THE MECHANISM OF ELECTROPHILIC FLUORINATIONS [J].
DIFFERDING, E ;
RUEGG, GM .
TETRAHEDRON LETTERS, 1991, 32 (31) :3815-3818
[2]   NUCLEOPHILIC-SUBSTITUTION VERSUS ELECTRON-TRANSFER .2. SN2 AT FLUORINE AND ELECTRON-TRANSFER ARE COMPETING AND DIFFERENT PATHWAYS IN ELECTROPHILIC FLUORINATIONS [J].
DIFFERDING, E ;
WEHRLI, M .
TETRAHEDRON LETTERS, 1991, 32 (31) :3819-3822
[3]   HETARYLATION OF C-NUCLEOPHILES - A NEW COURSE FOR THE REACTION OF N-FLUOROPYRIDINIUM SALTS WITH CARBANIONS [J].
GAKH, AA ;
KISELYOV, AS ;
SEMENOV, VV .
TETRAHEDRON LETTERS, 1990, 31 (50) :7379-7382
[4]  
GAKH AA, 1991, IAN SSSR KH, P2403
[5]  
GAKH AA, 1991, TETRAHEDRON, V47, P1615
[6]   CHLORINATION, BROMINATION, AND OXYGENATION OF THE PYRIDINE RING USING ACOF MADE FROM F2 [J].
HEBEL, D ;
ROZEN, S .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (05) :1123-1125
[7]  
KNIAZ K, IN PRESS J AM CHEM S
[8]   ELECTRONIC-STRUCTURES OF 1,2-C60X2N AND 1,4-C60X2N DERIVATIVES WITH N = 1, 2, 4, 6, 8, 10, 12, 18, 24, AND 30 [J].
MATSUZAWA, N ;
FUKUNAGA, T ;
DIXON, DA .
JOURNAL OF PHYSICAL CHEMISTRY, 1992, 96 (26) :10747-10756
[9]  
PAQUETTE LA, 1968, PRINCIPLES MODERN HE, P229
[10]   NO LUBRICANTS FROM FLUORINATED C-60 [J].
TAYLOR, R ;
AVENT, AG ;
DENNIS, TJ ;
HARE, JP ;
KROTO, HW ;
WALTON, DRM ;
HOLLOWAY, JH ;
HOPE, EG ;
LANGLEY, GJ .
NATURE, 1992, 355 (6355) :27-28