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Formation of novel sulfur-containing C60F16 cycloadducts between tetrathiafulvalene and C60F18; a unique six-electron cycloaddition of a fullerene involving F2 loss

Formation of novel sulfur-containing C60F16 cycloadducts between tetrathiafulvalene and C60F18; a unique six-electron cycloaddition of a fullerene involving F2 loss
Formation of novel sulfur-containing C60F16 cycloadducts between tetrathiafulvalene and C60F18; a unique six-electron cycloaddition of a fullerene involving F2 loss
Co-evaporation of solutions of C60F18 and tetrathiafulvalene in toluene produces an unsymmetrical C60F16:tetrathiafulvalene adduct through a unique six-electron cycloaddition involving displacement of two fluorine atoms by a terminal C=C double bond of the fulvalene. The adduct rearranges into two further adducts, one of which is characterised as a new type of fullerene derivative, a thiiranofullerene, formed by elimination of a thioketene moiety from the tetrathiafulvalene adduct. The initial addition also produces a bisadduct in which the addends comprise one tetrathiafulvalene molecule and one in which carbon disulfide has been eliminated. The latter adduct involves cyclo-addition of an unsaturated aromatic dithiolactone moiety.
aromaticity, cycloaddition, elimination, fullerenes, tetrathiafulvalene
0947-6539
2008-2012
Darwish, Adam D.
25f723f4-6a72-4e21-a361-76b275b617ef
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Boltalina, Olga V.
7fefd47c-6427-4d51-8d9f-e1b116daad8c
Gol'dt, Ilya
61109a1d-71d7-42e2-af9e-b4857a919ecf
Kuvytchko, Igor
5c228996-b937-40de-8618-931200aa8710
Da Ros, Tatiana
d8e9782d-524e-411f-ad18-21f6d6104a28
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6
Darwish, Adam D.
25f723f4-6a72-4e21-a361-76b275b617ef
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Boltalina, Olga V.
7fefd47c-6427-4d51-8d9f-e1b116daad8c
Gol'dt, Ilya
61109a1d-71d7-42e2-af9e-b4857a919ecf
Kuvytchko, Igor
5c228996-b937-40de-8618-931200aa8710
Da Ros, Tatiana
d8e9782d-524e-411f-ad18-21f6d6104a28
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6

Darwish, Adam D., Avent, Anthony G., Boltalina, Olga V., Gol'dt, Ilya, Kuvytchko, Igor, Da Ros, Tatiana, Street, Joan M. and Taylor, Roger (2003) Formation of novel sulfur-containing C60F16 cycloadducts between tetrathiafulvalene and C60F18; a unique six-electron cycloaddition of a fullerene involving F2 loss. Chemistry - A European Journal, 9 (9), 2008-2012. (doi:10.1002/chem.200204549).

Record type: Article

Abstract

Co-evaporation of solutions of C60F18 and tetrathiafulvalene in toluene produces an unsymmetrical C60F16:tetrathiafulvalene adduct through a unique six-electron cycloaddition involving displacement of two fluorine atoms by a terminal C=C double bond of the fulvalene. The adduct rearranges into two further adducts, one of which is characterised as a new type of fullerene derivative, a thiiranofullerene, formed by elimination of a thioketene moiety from the tetrathiafulvalene adduct. The initial addition also produces a bisadduct in which the addends comprise one tetrathiafulvalene molecule and one in which carbon disulfide has been eliminated. The latter adduct involves cyclo-addition of an unsaturated aromatic dithiolactone moiety.

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More information

Published date: 9 May 2003
Keywords: aromaticity, cycloaddition, elimination, fullerenes, tetrathiafulvalene

Identifiers

Local EPrints ID: 19942
URI: https://eprints.soton.ac.uk/id/eprint/19942
ISSN: 0947-6539
PURE UUID: c8697d28-33a6-47f6-bfb9-3e7c79fbd320

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Date deposited: 24 Feb 2006
Last modified: 15 Jul 2019 19:26

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Contributors

Author: Adam D. Darwish
Author: Anthony G. Avent
Author: Olga V. Boltalina
Author: Ilya Gol'dt
Author: Igor Kuvytchko
Author: Tatiana Da Ros
Author: Joan M. Street
Author: Roger Taylor

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