Chalcogenation of tetrathiafulvalene (TTF): synthesis of alkylthio-TTF and alkylseleno-TTF derivatives and X-ray crystal structure of ethylenediseleno TTF (EDS-TTF)
- 1 January 1993
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 13,p. 1403-1410
- https://doi.org/10.1039/p19930001403
Abstract
The reaction of mono-lithiated tetrathiafulvalene (TTF) with elemental sulfur or elemental selenium at –78 °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. Onepot 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.Keywords
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