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

The [4 + 2] cycloaddition of anthracene with C60F18: anthracene goes ring walking
The [4 + 2] cycloaddition of anthracene with C60F18: anthracene goes ring walking
From the [4+2] cycloaddition of anthracene at the curved face of C60F18 we have isolated two main isomers of C-s and C-1 symmetry (isomers 1 and 2, respectively) in ca. 3:2 relative yields; isomer 2 contained traces of a third isomer, also of C-s 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 C-s isomer (1) is reasonably stable, but the more crowded C-1 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 C-60 or C60Cl6 and anthracene) showing the fullerene cage acts here as an oxidant.
diels-alder adduct, c-60, fullerene
1364-5471
994-997
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Boltalina, Olga V.
7fefd47c-6427-4d51-8d9f-e1b116daad8c
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6
Wei, Xian-Wen
76b952ea-9f76-41de-be81-91f46652c927
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Boltalina, Olga V.
7fefd47c-6427-4d51-8d9f-e1b116daad8c
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6
Wei, Xian-Wen
76b952ea-9f76-41de-be81-91f46652c927

Avent, Anthony G., Boltalina, Olga V., Street, Joan M., Taylor, Roger and Wei, Xian-Wen (2001) The [4 + 2] cycloaddition of anthracene with C60F18: anthracene goes ring walking. Journal of the Chemical Society, Perkin Transactions 2, (6), 994-997. (doi:10.1039/b009441m).

Record type: Article

Abstract

From the [4+2] cycloaddition of anthracene at the curved face of C60F18 we have isolated two main isomers of C-s and C-1 symmetry (isomers 1 and 2, respectively) in ca. 3:2 relative yields; isomer 2 contained traces of a third isomer, also of C-s 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 C-s isomer (1) is reasonably stable, but the more crowded C-1 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 C-60 or C60Cl6 and anthracene) showing the fullerene cage acts here as an oxidant.

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More information

Published date: 2001
Keywords: diels-alder adduct, c-60, fullerene

Identifiers

Local EPrints ID: 19387
URI: https://eprints.soton.ac.uk/id/eprint/19387
ISSN: 1364-5471
PURE UUID: 47d86d3b-4673-447d-b8c0-95431e122238

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Date deposited: 13 Feb 2006
Last modified: 15 Jul 2019 19:27

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Contributors

Author: Anthony G. Avent
Author: Olga V. Boltalina
Author: Joan M. Street
Author: Roger Taylor
Author: Xian-Wen Wei

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