DIELS-ALDER ADDUCT OF C-60 AND 4-CARBOXY-O-QUINODIMETHANE - SYNTHESIS AND CHEMICAL-TRANSFORMATIONS

被引：59

作者：

BELIK, P ^{[1
]}

GUGEL, A ^{[1
]}

KRAUS, A ^{[1
]}

WALTER, M ^{[1
]}

MULLEN, K ^{[1
]}

机构：

[1] MAX PLANCK INST POLYMER RES,D-55128 MAINZ,GERMANY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 11期

关键词：

D O I：

10.1021/jo00116a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Diels-Alder reaction of o-quinodimethanes to buckminsterfullerene C-60 (1) affords thermally stable derivatives. 4-Carboxy-o-quinodimethane (4)was prepared in situ from 3,4-bis(bromomethyl)benzoic acid (3) and reacted with 1 to give the carboxy-substituted adduct mixture 5(n). Due to its decreased solubility, 5(rt) was used without further purification for transformations into the corresponding esters and amines. This was achieved by two different methods: (a) via the carboxylic acid chloride 6(n), whereby the alcohol/amine has to be used in excess, and (2) via the active ester 7(n = 1), which allows stoichiometric reactions with amines. All these derivatives are quite Soluble in commonly used organic solvents. This enabled us to separate and completly characterize the products.

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页码：3307 / 3310

页数：4

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