Fullerene-Based Macro-Heterocycle Prepared through Selective Incorporation of Three N and Two O Atoms into C60

A 14‐membered heterocycle is created on the C60 cage skeleton through a multistep procedure. Key steps involve repeated PCl5‐induced hydroxylamino N−O bond cleavage leading to insertion of nitrogen atoms, and also piperidine‐induced peroxo O−O bond cleavage leading to insertion of oxygen atoms. The...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2016-11, Vol.55 (47), p.14590-14594
Main Authors: Li, Yanbang, Zhang, Gaihong, Wang, Dian, Xu, Beidi, Xu, Dan, Lou, Ning, Gan, Liangbing
Format: Article
Language:English
Subjects:
copper complex
fullerenes
guanidine
heterocycles
macrocycle
Online Access:Get full text
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Summary:A 14‐membered heterocycle is created on the C60 cage skeleton through a multistep procedure. Key steps involve repeated PCl5‐induced hydroxylamino N−O bond cleavage leading to insertion of nitrogen atoms, and also piperidine‐induced peroxo O−O bond cleavage leading to insertion of oxygen atoms. The hetero atoms form one pyrrole, two pyran, and one diazepine rings in conjunction with the C60 skeleton carbon atoms. The fullerene‐based macrocycle showed unique reactivities towards fluoride ion and copper salts. N,O your product: A N,O‐heterocycle is created on the C60 cage skeleton through a multistep procedure, which includes repeated PCl5‐induced hydroxylamino N−O bond cleavage leading to insertion of nitrogen atoms, and also piperidine‐induced peroxo O−O bond cleavage leading to insertion of oxygen atoms. The fullerene based‐macrocycle showed unique reactivity towards fluoride ions and copper salts.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201606856