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Amination of [60]Fullerene by Ammonia and by Primary and Secondary Aliphatic Amines—Preparation of Amino[60]fullerene Peroxides
Author(s) -
Hu Xiangqing,
Jiang Zhongping,
Jia Zhenshan,
Huang Shaohua,
Yang Xiaobing,
Li Yuliang,
Gan Liangbing,
Zhang Shiwei,
Zhu Daoben
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200600932
Subject(s) - fullerene , primary (astronomy) , amination , ammonia , chemistry , organic chemistry , fullerene chemistry , amine gas treating , catalysis , physics , astronomy
Ammonia and aliphatic amines react readily in the oxygen‐rich regions of the C s symmetric fullerene peroxides C 60 (O)(OO t Bu) 4 ( 1 ) and C 60 (OH)(Br)(OO t Bu) 4 ( 2 c ). Michael addition‐type hydroamination of the 1,4‐diene moiety on the central skew‐pentagon was observed when 1 was treated with ammonia or with nonbulky primary amines, while sterically demanding primary amines opened the epoxy moiety to form vicinal aminohydroxy fullerene compounds with the amino group on the central pentagon. In 2 c the bromo group was replaced under similar conditions by ammonia and primary amines. Cyclic secondary amines showed different reaction patterns, forming hydrogenation products or aminoketal‐fullerenes when treated with 1 and 2 c , respectively. Single‐electron transfer (SET) is the key step in all the proposed mechanisms. The compounds were characterized by their spectroscopic data, and in addition, three single‐crystal X‐ray structures were obtained.