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

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).

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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