Issue 6, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

The [4 + 2] cycloaddition of anthracene with C60F18; anthracene goes ring walking

Anthony G. Avent,a   Olga V. Boltalina,b   Joan M. Street,c   Roger Taylor*a  and  Xian-Wen Weia  

* Corresponding authors

a The Chemistry Laboratory, CPES School, Sussex University, Brighton, UK

b Chemistry Department, Moscow State University, Moscow, Russia

c Chemistry Department, The University, Southampton, UK

Abstract

From the [4 + 2] cycloaddition of anthracene at the curved face of C60F18 we have isolated two main isomers of Cs and C1 symmetry (isomers 1 and 2, respectively) in ca. 3 ∶ 2 relative yields; isomer 2 contained traces of a third isomer, also of Cs symmetry. Of the four mono adducts that can, in principle, be formed by this cycloaddition, the yields of the three obtained reflect differences in steric hindrance between the fluorine and aromatic addends. The major Cs isomer (1) is reasonably stable, but the more crowded C1 isomer (2) reverts readily to C60F18 and anthracene on standing, and also undergoes rearrangement to isomer (1). This is the first example of spontaneous migration of a cycloaddend from one 6 ∶ 6-bond to another on the same fullerene cage surface. The UV/VIS spectrum of 1 is significantly different from that for C60F18, suggesting that some electronic interaction may exist between the addend and the cage. Anthraquinone is produced as a by-product of the reaction (and also from that between either C60 or C60Cl6 and anthracene) showing the fullerene cage acts here as an oxidant.

Graphical abstract: The [4 + 2] cycloaddition of anthracene with C60F18; anthracene goes ring walking

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Article information

DOI
https://doi.org/10.1039/B009441M
Article type
Paper
Submitted
24 Nov 2000
Accepted
06 Apr 2001
First published
02 May 2001

J. Chem. Soc., Perkin Trans. 2, 2001, 994-997

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The [4 + 2] cycloaddition of anthracene with C60F18; anthracene goes ring walking

A. G. Avent, O. V. Boltalina, J. M. Street, R. Taylor and X. Wei, J. Chem. Soc., Perkin Trans. 2, 2001, 994 DOI: 10.1039/B009441M

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