N-fluorobenzenesulfonimide based functionalization of C60
Yanbang Li1, Ning Lou, Liangbing Gan
1Beijing 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, China.
Organic Letters
|January 14, 2015
Summary
N-fluorobenzenesulfonimide reacts with C60 to form fullerene adducts. It also oxidizes cyclic amines, leading to novel tetraaminoaziridino adducts of C60.
Area of Science:
- Fullerene chemistry
- Organic synthesis
- Supramolecular chemistry
Background:
- Fullerenes (C60) are unique carbon allotropes with diverse applications.
- Functionalization of fullerenes is key to tailoring their properties.
- N-fluorobenzenesulfonimide (NFSI) is a versatile reagent in organic chemistry.
Purpose of the Study:
- To investigate the reaction of N-fluorobenzenesulfonimide (NFSI) with C60.
- To explore the utility of NFSI-C60 reaction products as precursors for fullerene adducts.
- To examine the oxidative capabilities of NFSI in fullerene functionalization reactions.
Main Methods:
- Reaction of C60 with N-fluorobenzenesulfonimide (NFSI).
- Synthesis of 1,2- and 1,4-bisfullerene adducts.
- Oxidation reactions involving C60, cyclic amines, and NFSI.
Main Results:
- NFSI reacts with C60 to yield products usable as precursors for bisfullerene adducts.
- NFSI acts as an oxidant in reactions of C60 with cyclic amines.
- Formation of tetraaminoaziridino adducts of C60 was achieved.
Conclusions:
- N-fluorobenzenesulfonimide is a valuable reagent for C60 functionalization.
- New pathways to complex fullerene adducts have been established.
- The dual role of NFSI as a reactant and oxidant expands its synthetic utility in fullerene chemistry.
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