Issue 7, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Some 4-fluorophenyl derivatives of [60]fullerene; spontaneous oxidation and oxide-induced fragmentation to C58

Adam D. Darwish,a   Anthony G. Avent,a   Paul R. Birkett,a   Harold W. Kroto,a   Roger Taylor*a  and  David R. M. Waltona  

* Corresponding authors

a School of Chemistry, Physics and Environmental Studies, University of Sussex, Brighton, UK

Abstract

The main products from the reaction of C60Cl6 with fluorobenzene–FeCl3 are C60(4-FC6H4)5Cl, 1,4-(4-FC6H4)2C60 (both of Cs symmetry) and asymmetric C60(4-FC6H4)4, accompanied by a small amount of C60(4-FC6H4)4H2. Exposure of the product to light and air before processing gives other components, including C60(4-FC6H4)4(4-FC6H3)O2, C60(4-FC6H4)5OH, and C60(4-FC6H4)6 (each of Cs symmetry), C60(4-FC6H4)4O2, C60(4-FC6H4)6O2, C60(4-FC6H4)7H, and C60(4-FC6H4)5H(OH)2/C60(4-FC6H4)5H. The formation of the oxides from air-exposed reaction products emphasises the need for atmospheric protection of fullerene derivatives. Fragmentation of the oxides during EI mass spectrometry occurs readily to give C58 and derivatives which must contain adjacent pentagons, stabilisation being derived from the presence of a heptagon.

Graphical abstract: Some 4-fluorophenyl derivatives of [60]fullerene; spontaneous oxidation and oxide-induced fragmentation to C58

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Article information

DOI
https://doi.org/10.1039/B102713C
Article type
Paper
Submitted
23 Mar 2001
Accepted
25 Apr 2001
First published
24 May 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 1038-1044

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Some 4-fluorophenyl derivatives of [60]fullerene; spontaneous oxidation and oxide-induced fragmentation to C58

A. D. Darwish, A. G. Avent, P. R. Birkett, H. W. Kroto, R. Taylor and D. R. M. Walton, J. Chem. Soc., Perkin Trans. 2, 2001, 1038 DOI: 10.1039/B102713C

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