Exohedral functionalization of [60]fullerene by [4+2] cycloadditions. Diels-Alder reactions of [60]fullerene with electron rich 2,3-dioxy-substituted-1,3-butadienes.

被引：36

作者：

TorresGarcia, G ^{[1
]}

Mattay, J ^{[1
]}

机构：

[1] UNIV MUNSTER,INST ORGAN CHEM,D-48149 MUNSTER,GERMANY

来源：

TETRAHEDRON | 1996年 / 52卷 / 15期

关键词：

60]fullerene; Diels-Alder reaction; 2,3-dioxybutadienes; acyloin;

D O I：

10.1016/0040-4020(96)00172-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder reactions between [60]fullerene and 2,3-dimethylene-1,4-dioxane (1) or 4,5-dimethylene-2,2-dimethyldioxolane (2) are described. The C-60:1 derivative was obtained under mild thermal conditions. The compound 2 necessitates the use of high pressure to perform the [4+2] cycloaddition and its hydrolysis yields the acyloin derivative 7. Copyright (C) 1996 Published by Elsevier Science Ltd

引用

页码：5421 / 5426

页数：6

共 12 条

[1] SYNTHESIS OF 1,2-(2,3-DIHYDRO-1H-AZIRINO)-[60]FULLERENE, THE PARENT FULLEROAZIRIDINE [J].

AVERDUNG, J ;

LUFTMANN, H ;

MATTAY, J ;

CLAUS, KU ;

ABRAHAM, W .

TETRAHEDRON LETTERS, 1995, 36 (17) :2957-2958

[2]

AVERDUNG J, 1995, PHYSICS CHEM FULLERE, P137

[3]

AVERDUNG J, 1994, TETRAHEDRON, V51, P2543

[4] SEQUENTIAL DOUBLE-MICHAEL ADDITIONS OF DIENOLATES WITH C-60 - RAPID ACCESS TO STERICALLY CONGESTED BUCKMINSTERFULLERENE DERIVATIVES WITH DEFINED STEREOCHEMISTRY [J].

GANAPATHI, PS ;

FRIEDMAN, SH ;

KENYON, GL ;

RUBIN, Y .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (10) :2954-2955

[5]

HIRSCH A, 1995, SYNTHESIS-STUTTGART, P895

[6]

Hirsch A, 1994, CHEM FULLERENES

[7] A HIGHLY SYMMETRICAL SIXFOLD CYCLOADDITION PRODUCT OF FULLERENE C-60 [J].

KRAUTLER, B ;

MAYNOLLO, J .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (01) :87-88

[8]

KRAUTLER B, 1993, HELV CHIM ACTA, V76, P1626

[9]

KRAUTLER B, 1995, ANGEW CHEM, V107, P69

[10]

Lamparth I., 1995, ANGEW CHEM, V107, P1755

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