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Formation of Novel Sulfur‐Containing C 60 F 16 Cycloadducts between Tetrathiafulvalene and C 60 F 18 ; A Unique Six‐Electron Cycloaddition of a Fullerene Involving F 2 Loss
Author(s) -
Darwish Adam D.,
Avent Anthony G.,
Boltalina Olga V.,
Gol′dt Ilya,
Kuvytchko Igor,
Da Ros Tatiana,
Street Joan M.,
Taylor Roger
Publication year - 2003
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200204549
Subject(s) - tetrathiafulvalene , cycloaddition , adduct , moiety , chemistry , derivative (finance) , medicinal chemistry , stereochemistry , molecule , photochemistry , organic chemistry , catalysis , financial economics , economics
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 CC 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.