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Published on: March 20, 2017
Inverse Electron Demand Diels-Alder Reaction on M3N@C80 (M=Lu, Sc): Reactivity and Reversibility Enable Chemical
Yue Sun1, Laura Abella2, Thomas J Emge1
1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, 123 Bevier Rd, Piscataway, NJ 08854, USA.
Abstract:
Endohedral metallofullerenes are chemically more inert compared to empty fullerenes, primarily due to their intramolecular electron transfer. In this work, we report an inverse electron demand Diels-Alder (IEDDA) reaction on M3N@C80 (M=Lu, Sc), where they show significantly higher reactivity than empty fullerenes. The molecular structures of the [4+2] cycloadducts were unambiguously characterized. Moreover, the cycloadducts can fully revert to pristine M3N@C80 via retro-cycloaddition upon thermal treatment. With the unusual reactivity and reversibility, the IEDDA reaction enables an effective separation approach for metallofullerenes from their soot extracts, opening path to efficient and economical scale-up synthesis of metallofullerenes in laboratory and industrial settings.
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