First isolation and characterization of eight regioisomers for [60]fullerene-benzyne bisadducts

被引:77
作者
Nakamura, Y
Takano, N
Nishimura, T
Yashima, E
Sato, M
Kudo, T
Nishimura, J [1 ]
机构
[1] Gunma Univ, Dept Chem, Kiryu, Gumma 3768515, Japan
[2] Nagoya Univ, Grad Sch Engn, Dept Mol Design & Engn, Chikusa Ku, Nagoya, Aichi 4648603, Japan
关键词
D O I
10.1021/ol0156547
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The [2 + 2] cycloaddition between [60]fullerene and benzyne generated from 4,5-dimethoxyanthranilic acid (4) afforded bisadducts 5 along with the monoadduct. All of the eight possible regioisomers were first isolated by HPLC and then characterized on the basis of MS, NMR, UV-vis, and CD spectroscopies.
引用
收藏
页码:1193 / 1196
页数:4
相关论文
共 19 条
[1]   OXIDATION OF BUCKMINSTERFULLERENE WITH M-CHLOROPEROXYBENZOIC ACID - CHARACTERIZATION OF A C-S ISOMER OF THE DIEPOXIDE C60O2 [J].
BALCH, AL ;
COSTA, DA ;
NOLL, BC ;
OLMSTEAD, MM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (35) :8926-8932
[2]   Differentiation of isomers resulting from bisaddition to C-60 using He-3 NMR spectrometry [J].
Cross, RJ ;
JimenezVazquez, HA ;
Lu, Q ;
Saunders, M ;
Schuster, DI ;
Wilson, SR ;
Zhao, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (46) :11454-11459
[3]   Additions of azomethine ylides to fullerene C60 assisted by a removable anchor [J].
Da Ros, T ;
Prato, M ;
Lucchini, V .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (14) :4289-4297
[4]   Templated regioselective and stereoselective synthesis in fullerene chemistry [J].
Diederich, F ;
Kessinger, R .
ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (06) :537-545
[5]   Regiochemistry of twofold additions to [6,6] bonds in C-60: Influence of the addend-independent cage distortion in 1,2-monoadducts [J].
Djojo, F ;
Herzog, A ;
Lamparth, I ;
Hampel, F ;
Hirsch, A .
CHEMISTRY-A EUROPEAN JOURNAL, 1996, 2 (12) :1537-1547
[6]   Enantiomeric separation of [60]fullerene derivatives with an inherent chiral addition pattern [J].
Gross, B ;
Schurig, V ;
Lamparth, I ;
Herzog, A ;
Djojo, F ;
Hirsch, A .
CHEMICAL COMMUNICATIONS, 1997, (12) :1117-1118
[7]   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
[8]  
Hirsch A, 1999, TOP CURR CHEM, V199, P1
[9]   REACTION OF FULLERENES AND BENZYNE [J].
HOKE, SH ;
MOLSTAD, J ;
DILETTATO, D ;
JAY, MJ ;
CARLSON, D ;
KAHR, B ;
COOKS, RG .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (19) :5069-5071
[10]   Saccharide libraries as potential templates for regio- and chiroselective introduction of two functional groups into [60]fullerene [J].
Ishi-i, T ;
Nakashima, K ;
Shinkai, S ;
Ikeda, A .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (03) :984-990