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Synlett 2000; 2000(9): 1318-1320
DOI: 10.1055/s-2000-7162
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Heterocyclization of [60]Fullerene with Isocyanides

Y. Tsunenishi* , H. Ishida, K. Itoh, M. Ohno
  • *Department of Molecular Design and Engineering, Graduate School of Engineering, Nagoya University, Chikusa, Nagoya 464-8603, Japan
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Publication Date:
31 December 2000 (online)

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Isocyanides cycloadded to a double bond of [60]fullerene to give various [60]fullero-1-pyrrolines. While the reaction with unsubstituted ethyl isocyanoacetate occurred slowly even without a catalyst, it was facilitated with NEt3, and use of DBU was more effective for α-monosubstituted isocyanoacetates. Alternatively, copper(I) oxide was found to be an expedient catalyst, which allowed the possible use of an unactivated isocyanide such as PhCH2NC as well as other activated isocyanides.

[60]fullerene - isocyanide - 1-pyrroline - cycloaddition - catalytic reaction