The reaction of mono-lithiated tetrathiafulvalene (TTF) with elemental sulfur or elemental selenium at -78-degrees-C yields the transient species TTF-S- Li+ and TTF-Se- Li+, respectively, which have been trapped with a range of alkyl halides to yield new alkylthio- and alkylseleno-TTF derivatives. Reaction of the TTF-thiolate anion with 2-bromoethanol yields 4-(2-hydroxyethylthio)tetrathiafulvalene which is a particularly versatile building block for the synthesis of a range of new mono-functionalised TTF derivatives containing ether, ester, acrylate, urethane and vinylthio groups in the side chain. One-pot syntheses of ethylenedithio-TTF (EDT-TTF) and ethylenediseleno-TTF (EDS-TTF) from TTF are reported. The structure of EDS-TTF has been determined by single crystal X-ray analysis which reveals dimers with molecular planes orthogonal to each other.
|Number of pages||7|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|Publication status||Published - 7 Jul 1993|
- organic metals
Moore, A. J., Bryce, M. R., Cooke, G., Marshallsay, G. J., Skabara, P. J., Batsanov, A. S., ... Daley, S. T. A. K. (1993). Chalcogenation of tetrathiafulvalene (TTF): synthesis of alkylthio-TTF and alkylseleno-TTF derivatives and X-ray crystal structure of ethylenediseleno TTF (EDS-TTF). Journal of the Chemical Society, Perkin Transactions 1, 1993(1), 1403-1410. https://doi.org/10.1039/P19930001403