Issue 12, 2013

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

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

Supplementary files

Article information

Article type
Communication
Submitted
21 Nov 2012
Accepted
14 Dec 2012
First published
17 Dec 2012

Chem. Commun., 2013,49, 1220-1222

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements