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Issue 12, 2013
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Electrochemical control of the regioselectivity in the exohedral functionalization of C60: the role of aromaticity

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Abstract

In this work we show that the regioselectivity of the Diels–Alder, 1,3-dipolar, and carbene cycloadditions to C60 changes from the usual [6,6] addition in neutral species to the [5,6] attack when the number of electrons added to the fullerenic cage increases. Changes in the aromaticity of the five- and six-membered rings of C60 during the reduction process provide a rationale to understand this regioselectivity change.

Graphical abstract: Electrochemical control of the regioselectivity in the exohedral functionalization of C60: the role of aromaticity

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Publication details

The article was received on 21 Nov 2012, accepted on 14 Dec 2012 and first published on 17 Dec 2012


Article type: Communication
DOI: 10.1039/C2CC38390J
Citation: Chem. Commun., 2013,49, 1220-1222
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    Electrochemical control of the regioselectivity in the exohedral functionalization of C60: the role of aromaticity

    M. Garcia-Borràs, S. Osuna, M. Swart, J. M. Luis and M. Solà, Chem. Commun., 2013, 49, 1220
    DOI: 10.1039/C2CC38390J

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