SYNTHESIS AND ELECTROCHEMICAL COMPLEXATION STUDIES OF 1,8-BIS(AZACROWN ETHER)ANTHRAQUINONES

被引：11

作者：

ECHEGOYEN, L ^{[1
]}

LAWSON, RC ^{[1
]}

LOPEZ, C ^{[1
]}

DEMENDOZA, J ^{[1
]}

HAFEZ, Y ^{[1
]}

TORRES, T ^{[1
]}

机构：

[1] UNIV AUTONOMA MADRID,DEPT QUIM,E-28049 MADRID,SPAIN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 14期

关键词：

D O I：

10.1021/jo00093a013

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 1,8-difluoroanthraquinone with aza-12-crown-4 and aza-15-crown-5 in DMF at 50 degrees C affords the disubstituted anthraquinones 6 and 7 in good yields. A similar methodology has been used to prepare the lipophilic diaza-12-crown-4 anthraquinone systems 12-14. Compounds 6 and 7 exhibit enhanced sodium and lithium binding upon electrochemical reduction to the corresponding mono- and dianions. Both 6 and 7 form 1:1 complexes with Na+. However, with the smaller Li+ cation, both compounds form 1:2 ligand:Li+ complexes. Cation binding enhancements for Li+ and Na+ are very large with K-2/K-1 values as high as 10(5).

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页码：3814 / 3820

页数：7

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