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Synthesis 1991; 1991(4): 263-265
DOI: 10.1055/s-1991-26439
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Halogenation of Tetrathiafulvalene

Martin R. Bryce* , Graeme Cooke
  • *Department of Chemistry, University of Durham, Durham, DH1 3LE, England
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Publication Date:
29 April 2002 (online)

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Monolithiation of tetrathiafulvalene (2-(1,3-dithiol-2-ylidene)-1,3-dithiole, TTF) followed by reaction with the appropriate p-toluenesulphonyl halide yields monochloro-, monobromo- and monoiodo-TTF (34-48 % yield); tetrachloro-TTF is obtained in 30 % yield by tetralithiation of TTF followed by addition of p-toluenesulphonyl chloride. Cyclic voltammetric data establish that the oxidation potential of TTF is significantly increased upon halogenation.