Synthesis 2018; 50(21): 4283-4289
DOI: 10.1055/s-0037-1610220
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Pentapyrazolyl, Pentapyrrolyl, and Pentaanilino C60 Derivatives

Ning Lou
a   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. of China   Email: gan@pku.edu.cn
,
Olga A. Kraevaya
b   Institute 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*
b   Institute for Problems of Chemical Physics of Russian Academy of Sciences, Semenov Prospect 1, Chernogolovka, Moscow Region, 142432, Russian Federation   Email: troshin2003@inbox.ru
c   Skolkovo Institute of Science and Technology, Nobel St. 3, Moscow, 143026, Russian Federation
,
Liangbing Gan*
a   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. of China   Email: gan@pku.edu.cn
d   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Shanghai 200032, P. R. of China
› Author Affiliations
Financial support was provided by NNSFC (Grant 21672009), MOST (2015CB856600) and RFBR (grant No. 16-53-52030).
Further Information

Publication History

Received: 14 June 2018

Accepted after revision: 03 July 2018

Publication Date:
25 July 2018 (online)


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.

Supporting Information

 
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