Preparation and characterization of six bis(N-methylpyrrolidine)-C-60 isomers: Magnetic deshielding in isomeric bisadducts of C-60

被引：110

作者：

Lu, Q ^{[1
]}

Schuster, DI ^{[1
]}

Wilson, SR ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 14期

关键词：

D O I：

10.1021/jo960466t

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of isomers of bis(N-methylpyrrolidine)-C-60 2 (Prato bisadducts) was prepared by the 1,3-dipolar cycloaddition of N-methylazomethine ylide to C-60. Six isomers were separated and characterized by ESI-MS, UV/vis, and H-1 and C-13 NMR spectroscopy. The structures of these bisadducts were assigned based on (1) comparison of their molecular symmetries with their 1H and C-13 MMR spectra, (2) comparison of their UV/vis spectra with those of corresponding Bingel-Hirsch bisadducts, and (3) the order of deshielding of the methylene and N-methyl H-1 NMR resonances. Prate bisaddition is less chemoselective than Bingel-Hirsch bisaddition to C-60.

引用

页码：4764 / 4768

页数：5

共 27 条

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