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Stereoselective synthesis of amino-substituted cyclopentafullerenes promoted by magnesium perchlorate/ferric perchlorate

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Abstract

A facile one-step reaction of [60]fullerene with cinnamaldehydes and amines promoted by magnesium perchlorate/ferric perchlorate under air conditions afforded a series of rare amino-substituted cyclopentafullerenes in moderate to good yields. Stereoselectivity was readily achieved. Secondary amines exclusively produced N,N-disubstituted cyclopentafullerenes as cis isomers, while arylamines gave N-monosubstituted cyclopentafullerenes with a preference of cis isomers as major products. N-Monosubstituted cyclopentafullerenes could be further converted into other scarce cyclopentafullerenes in the presence of acid chloride or paraformaldehyde. A possible reaction pathway was proposed to elucidate the formation of amino-substituted cyclopentafullerenes.

Graphical abstract: Stereoselective synthesis of amino-substituted cyclopentafullerenes promoted by magnesium perchlorate/ferric perchlorate

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Article information


Submitted
17 Oct 2019
Accepted
03 Jan 2020
First published
13 Jan 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Stereoselective synthesis of amino-substituted cyclopentafullerenes promoted by magnesium perchlorate/ferric perchlorate

W. Ma, K. Wang, C. Huang, H. Wang, F. Li, R. Sun, L. Liu, C. Liu and A. M. Asiri, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02248A

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