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[2+1] Cycloaddition of Nitrene onto C 60 Revisited: Interconversion between an Aziridinofullerene and an Azafulleroid
Author(s) -
Nakahodo Tsukasa,
Okada Mitsunori,
Morita Hiroyuki,
Yoshimura Toshiaki,
Ishitsuka Midori O.,
Tsuchiya Takahiro,
Maeda Yutaka,
Fujihara Hisashi,
Akasaka Takeshi,
Gao Xingfa,
Nagase Shigeru
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200704410
Subject(s) - nitrene , cycloaddition , chemistry , yield (engineering) , fullerene , catalysis , organic chemistry , physics , thermodynamics
An open and closed case : The reversible interconversion of a [1,2]aziridinofullerene and a [1,6]azafulleroid represents the first such example for a monosubstituted fullerene. While the [1,2]aziridinofullerene rearranges thermally to the [1,6]azafulleroid, the [1,6]azafulleroid rearranges photochemically to the [1,2]aziridinofullerene in high yield (see picture).