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

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

© Chemical Communications, 2013, vol. 49, p. 1220-1222

Royal Society of Chemistry (RSC)

Author: Garcia Borràs, Marc
Osuna Oliveras, Sílvia
Swart, Marcel
Luis Luis, Josep Maria
Solà i Puig, Miquel
Date: 2013
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
Format: application/pdf
ISSN: 1359-7345 (versió paper)
1364-548X (versió electrònica)
Document access: http://hdl.handle.net/10256/10206
Language: eng
Publisher: Royal Society of Chemistry (RSC)
Collection: MICINN/PN 2012-2014/CTQ2011-23156
MICINN/PN 2012-2014/CTQ2011-25086
AGAUR/2009-2014/2009 SGR-637
AGAUR/2009-2014/2009 SGR-528
Reproducció digital del document publicat a: http://dx.doi.org/10.1039/c2cc38390j
Articles publicats (D-Q)
info:eu-repo/grantAgreement/EC/FP7/252856
Is part of: © Chemical Communications, 2013, vol. 49, p. 1220-1222
Rights: Tots els drets reservats
Subject: Diels-Alder, Reacció de
Diels-Alder reaction
Reaccions químiques regioselectives
Regioselectivity Chemical reactions
Fullerenes
Ful·lerens
Aromaticitat (Química)
Aromaticity (Chemistry)
Title: Electrochemical control of the regioselectivity in the exohedral functionalization of C60: The role of aromaticity
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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