Selective deletion of one carbon atom from C60 through benzylamine mediated reactions

Yaqiong Wang; Yiran Wu; Yuming Yu; Jie Su; Yi Qiu; Liangbing Gan

doi:10.1039/D4QO00449C

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Selective deletion of one carbon atom from C₆₀ through benzylamine mediated reactions†‡

Yaqiong Wang,^ab Yiran Wu,^ab Yuming Yu,*^ab Jie Su,*^ab Yi Qiu^ab and Liangbing Gan

*^ab

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* Corresponding authors

^a State Key Laboratory of Chemistry and Utilization of Carbon-Based Energy Resources, College of Chemistry, Xinjiang University, 830017 Urumqi, Xinjiang, P. R. China
E-mail: yym2009@iccas.ac.cn, jie.su@pku.edu.cn, gan@pku.edu.cn

^b Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, P. R. China

Abstract

Selective deletion of carbon atom(s) from spherical skeletons results in norfullerene derivatives. Among the numerous fullerene derivatives, norfullerenes are still quite rare. In the present work benzylamine has been found to react with a [60]fullerene-mixed peroxide derivative with a 9-membered orifice. Subsequent transformations of the benzylamine-added product afforded a nor[59]fullerene derivative with an 11-membered orifice. The carbon atom deletion process involves an intramolecular hydrogen atom transfer and decarboxylation sequence.

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Article information

DOI: https://doi.org/10.1039/D4QO00449C
Article type: Research Article
Submitted: 11 Mar 2024
Accepted: 31 Mar 2024
First published: 10 Apr 2024

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Org. Chem. Front., 2024,11, 3026-3032

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Selective deletion of one carbon atom from C₆₀ through benzylamine mediated reactions

Y. Wang, Y. Wu, Y. Yu, J. Su, Y. Qiu and L. Gan, Org. Chem. Front., 2024, 11, 3026 DOI: 10.1039/D4QO00449C

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