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Regioselective cycloaddition of La2@I(h)-C80 with tetracyanoethylene oxide: formation of an endohedral dimetallofullerene adduct featuring enhanced electron-accepting character



Regioselective cycloaddition of La2@I(h)-C80 with tetracyanoethylene oxide: formation of an endohedral dimetallofullerene adduct featuring enhanced electron-accepting character



Journal of the American Chemical Society 133(11): 3796-3799



We describe the regioselective cycloaddition of La(2)@I(h)-C(80) with tetracyanoethylene oxide (TCNEO), which enabled the formation of the corresponding adduct having a tetracyanotetrahydrofuran moiety. X-ray crystallographic analysis revealed that the cycloaddition took place as a [5,6] addition. Along with dynamic swing motion of the metal atoms, the results of this electrochemical study demonstrate that TCNEO addition enhanced the electron-accepting character of La(2)@I(h)-C(80) and that the first reduction potential of the adduct reached -0.21 V versus the ferrocene/ferrocenium couple, which is the lowest value reported for endohedral metallofullerenes and their derivatives to date.

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Accession: 055445606

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PMID: 21351732

DOI: 10.1021/ja2000243



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