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Selective Nitration of Open‐Cage [60]Fullerene Derivatives by Ponzio Reaction
Author(s) -
Zhang Hao,
Gao Rui,
Liu Zhen,
Wang Xiaoge,
Su Jie,
Gan Liangbing
Publication year - 2021
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202100557
Subject(s) - chemistry , nitration , hydroxylamine , oxime , cage , derivative (finance) , reactivity (psychology) , nitro , medicinal chemistry , organic chemistry , photochemistry , financial economics , medicine , alkyl , alternative medicine , mathematics , pathology , combinatorics , economics
The carbonyl group on the rim of open‐cage C 60 derivative was converted into an oxime group when treated with hydroxylamine. Nitrogen tetroxide could convert the oxime group into gem ‐dinitro groups, similar to the Ponzio reaction of classical organic compounds. Single crystal X‐ray diffraction data shows that one of the nitro group is directly above the orifice acting as an effective stopper. Presence of the gem ‐dinitro groups also showed significant effect on the reactivity of other functional groups on the rim of the orifice.