Synthesis of fluorous fullerene adducts: Reversible solubilization of fullerenes in perfluorinated solvents

被引：22

作者：

Wilson, SR ^{[1
]}

Yurchenko, ME

Schuster, DI

Khong, A

Saunders, M

机构：

[1] NYU, Dept Chem, New York, NY 10003 USA

[2] Yale Univ, Dept Chem, New Haven, CT 06511 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 09期

关键词：

D O I：

10.1021/jo991008y

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fullerene (C-60) Diels-Alder adducts with perfluoroalkylated 1,3-cyclopentadiene (1a,b) were synthesized and studied. The perfluoroalkylated cyclopentadiene was found to be less reactive toward C-60 than cyclopentadiene itself, possibly because of the electron-withdrawing effect of the side chain. Because of the same effect, the temperature of the retro-Diels-Alder reaction for the fluorinated adducts was lower (70 degrees C) than the reported value (95 degrees C) for the cyclopentadiene adducts of C-60. Higher adducts of the fluorous diene and C-60 were found to be soluble in perfluorohexane and to show visible partitioning between organic (toluene) and fluorous phases. Also, the Diels-Alder addition of the fluorous diene was accompanied by extensive oxidation of the fullerene core, as revealed by MALDI-TOF data.

引用

页码：2619 / 2623

页数：5

共 18 条

[1] Differentiation of isomers resulting from bisaddition to C-60 using He-3 NMR spectrometry [J].