Synthesis of Pentapyrazolyl, Pentapyrrolyl, and Pentaanilino C60 Derivatives

Ning Lou; Olga A. Kraevaya; Pavel A. Troshin; Liangbing Gan

doi:10.1055/s-0037-1610220

Synthesis, Table of Contents

Synthesis 2018; 50(21): 4283-4289
DOI: 10.1055/s-0037-1610220

paper

Synthesis of Pentapyrazolyl, Pentapyrrolyl, and Pentaanilino C₆₀ Derivatives

Authors

Ning Lou

^aBeijing 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. of China Email: gan@pku.edu.cn
Olga A. Kraevaya

^bInstitute for Problems of Chemical Physics of Russian Academy of Sciences, Semenov Prospect 1, Chernogolovka, Moscow Region, 142432, Russian Federation Email: troshin2003@inbox.ru
Pavel A. Troshin*

^bInstitute for Problems of Chemical Physics of Russian Academy of Sciences, Semenov Prospect 1, Chernogolovka, Moscow Region, 142432, Russian Federation Email: troshin2003@inbox.ru

^cSkolkovo Institute of Science and Technology, Nobel St. 3, Moscow, 143026, Russian Federation
Liangbing Gan*

^aBeijing 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. of China Email: gan@pku.edu.cn

^dState Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China

Abstract

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Abstract

Unlike the facile addition of aliphatic amines to fullerenes, heteroaromatic compounds with NH group do not react directly with pristine fullerenes. The present work reports the preparation of several cyclopentadienyl type [60]fullerene derivatives with pyrazole and pyrrole addends through replacement reactions of C₆₀Cl₆ in the presence of tetrabutylammonium bromide. The method has also been applied for the synthesis of aniline and methoxyamine [60]fullerene cyclopentadienyl type adducts. Radical species were involved in the reaction mechanism.

Key words

fullerene - amination - pyrrole - substituent effect - nucleophilic aromatic substitution

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References

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19 CCDC 1843599 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

Supplementary Material

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