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Darwish AD, Avent AG, Boltalina OV, et al. Formation of novel sulfur-containing C60F16 cycloadducts between tetrathiafulvalene and C60F18; a unique six-electron cycloaddition of a fullerene involving F2 loss. Chemistry. 2003;9(9):2008-12doi: 10.1002/chem.200204549.
Darwish, A. D., Avent, A. G., Boltalina, O. V., Gol'dt, I., Kuvytchko, I., Da Ros, T., Street, J. M., & Taylor, R. (2003). Formation of novel sulfur-containing C60F16 cycloadducts between tetrathiafulvalene and C60F18; a unique six-electron cycloaddition of a fullerene involving F2 loss. Chemistry (Weinheim an der Bergstrasse, Germany), 9(9), 2008-12. https://doi.org/10.1002/chem.200204549
Darwish, Adam D, et al. "Formation of novel sulfur-containing C60F16 cycloadducts between tetrathiafulvalene and C60F18; a unique six-electron cycloaddition of a fullerene involving F2 loss." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 9,9 (2003): 2008-12. doi: https://doi.org/10.1002/chem.200204549
Darwish AD, Avent AG, Boltalina OV, Gol'dt I, Kuvytchko I, Da Ros T, Street JM, Taylor R. Formation of novel sulfur-containing C60F16 cycloadducts between tetrathiafulvalene and C60F18; a unique six-electron cycloaddition of a fullerene involving F2 loss. Chemistry. 2003 May 09;9(9):2008-12. doi: 10.1002/chem.200204549. PMID: 12740847.
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Chemistry. 2003 May 09;9(9):2008-12. doi: 10.1002/chem.200204549.

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

Chemistry (Weinheim an der Bergstrasse, Germany)

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

Affiliations

  1. The Chemistry Laboratory, CPES School, Sussex University, Brighton BN1 9QJ, UK.

PMID: 12740847 DOI: 10.1002/chem.200204549

Abstract

Co-evaporation of solutions of C(60)F(18) and tetrathiafulvalene in toluene produces an unsymmetrical C(60)F(16):tetrathiafulvalene adduct through a unique six-electron cycloaddition involving displacement of two fluorine atoms by a terminal Cdbond;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 cycloaddition of an unsaturated aromatic dithiolactone moiety.

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