Synthesis of methano[60]fullerene derivatives: the fluoride ion-mediated reaction of [60]fullerene with silylated nucleophiles

被引:13
作者
Hino, T [1 ]
Kinbara, K [1 ]
Saigo, K [1 ]
机构
[1] Univ Tokyo, Grad Sch Frontier Sci, Dept Integrated Biosci, Bunkyo Ku, Hongo, Tokyo 1138656, Japan
关键词
fullerenes; cyclopropanation; ketene acetals; enol ether;
D O I
10.1016/S0040-4039(01)00943-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new reaction of [60]fullerene with silylated nucleophiles is described. The cyclopropanation of [60]fullerene with silylated nucleophiles, such as silyl ketene acetals. silyl ketene thioacetals. and silyl enol ethers, derived from alpha -halo carbonyl compounds, smoothly proceeded in the presence of KF/18-crown-6 to give the corresponding methano[60]fullerene derivatives in moderate to good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5065 / 5067
页数:3
相关论文
共 25 条
[1]   FULLERENE-ACETYLENE HYBRIDS - ON THE WAY TO SYNTHETIC MOLECULAR CARBON ALLOTROPES [J].
ANDERSON, HL ;
FAUST, R ;
RUBIN, Y ;
DIEDERICH, F .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (13) :1366-1368
[2]   6,6-BRIDGED CLOSED METHANOFULLERENES FROM C-60 AND PHOSPHONIUM YLIDES [J].
BESTMANN, HJ ;
HADAWI, D ;
RODER, T ;
MOLL, C .
TETRAHEDRON LETTERS, 1994, 35 (48) :9017-9020
[3]   CYCLOPROPYLATION OF FULLERENES [J].
BINGEL, C .
CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (08) :1957-1959
[4]   Efficient cyclopropanation of C-60 starting from malonates [J].
Camps, X ;
Hirsch, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11) :1595-1596
[5]   SYNTHESES, STRUCTURES, AND PROPERTIES OF METHANOFULLERENES [J].
DIEDERICH, F ;
ISAACS, L ;
PHILP, D .
CHEMICAL SOCIETY REVIEWS, 1994, 23 (04) :243-255
[6]   Covalent fullerene chemistry [J].
Diederich, F ;
Thilgen, C .
SCIENCE, 1996, 271 (5247) :317-323
[7]   ELECTROCHEMICALLY INDUCED ISOMERIZATION OF A FULLEROID TO A METHANOFULLERENE [J].
EIERMANN, M ;
WUDL, F ;
PRATO, M ;
MAGGINI, M .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (18) :8364-8365
[8]   Stereochemical control in organic synthesis using silicon-containing compounds [J].
Fleming, I ;
Barbero, A ;
Walter, D .
CHEMICAL REVIEWS, 1997, 97 (06) :2063-2192
[9]   FULLERENE CHEMISTRY IN 3 DIMENSIONS - ISOLATION OF 7 REGIOISOMERIC BISADDUCTS AND CHIRAL TRISADDUCTS OF C-60 AND DI(ETHOXYCARBONYL)METHYLENE [J].
HIRSCH, A ;
LAMPARTH, I ;
KARFUNKEL, HR .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1994, 33 (04) :437-438
[10]  
HIRSCH A, 1995, SYNTHESIS-STUTTGART, P895