A SUPERIOR SYNTHESIS OF [6,6]-METHANOFULLERENES - THE REACTION OF SULFONIUM YLIDES WITH C-60

被引：75

作者：

WANG, YH ^{[1
]}

CAO, JR ^{[1
]}

SCHUSTER, DI ^{[1
]}

WILSON, SR ^{[1
]}

机构：

[1] NYU,DEPT CHEM,NEW YORK,NY 10003

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 38期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1016/0040-4039(95)01443-L

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition-elimination reaction of stabilized sulfonium ylides 1a-f to C-60 provides a new high yield route to [6,6]-methanofullerenes. The rates of reaction differ with the nucleophilicity of the ylides.

引用

页码：6843 / 6846

页数：4

共 30 条

[1] SYNTHESIS AND CHARACTERIZATION OF DIETHYNYLMETHANOBUCKMINSTERFULLERENE, A BUILDING-BLOCK FOR MACROCYCLIC AND POLYMERIC CARBON ALLOTROPES [J].

AN, YZ ;

RUBIN, Y ;

SCHALLER, C ;

MCELVANY, SW .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (11) :2927-2929

[2] METHANOFULLERENES AND METHANOFULLEROIDS HAVE DIFFERENT ELECTROCHEMICAL-BEHAVIOR AT NEGATIVE POTENTIALS [J].

ARIAS, F ;

ECHEGOYEN, L ;

WILSON, SR ;

LU, Q ;

LU, QY .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (04) :1422-1427

[3] 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

[4] CYCLOPROPYLATION OF FULLERENES [J].

BINGEL, C .

CHEMISCHE BERICHTE-RECUEIL, 1993, 126 (08) :1957-1959

[5]

BOUTORINE AS, 1994, ANGEW CHEM INT EDIT, V33, P2462

[6]

DIEDERICH F, 1994, CHEM SOC REV, P243

[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] THE SPECIFIC ACID-CATALYZED AND PHOTOCHEMICAL ISOMERIZATION OF A ROBUST FULLEROID TO A METHANOFULLERENE [J].

GONZALEZ, R ;

HUMMELEN, JC ;

WUDL, F .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (08) :2618-2620

[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] REGIOCHEMISTRY OF MULTIPLE ADDITIONS TO THE FULLERENE CORE - SYNTHESIS OF A T-H-SYMMETRICAL HEXAKISADDUCT OF C-60 WITH BIS(ETHOXYCARBONYL)METHYLENE [J].

HIRSCH, A ;

LAMPARTH, I ;

GROSSER, T ;

KARFUNKEL, HR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (20) :9385-9386

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