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Synthesis 1997; 1997(6): 617-619
DOI: 10.1055/s-1997-1407
short paper
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Direct Syntheses of Tetrathiafulvalene and Bis(ethylenedithio)tetrathiafulvalene By a Non-Coupling Route from 1,4,5,8-Tetrathianaphthalene

Ronald L. Meline, Ronald L. Elsenbaumer*
  • *Department of Chemistry and Biochemistry, The University of Texas at Arlington, Texax 76019, USA, Fax +1(817)2723808; E-mail: elsenbaumer@uta.edu
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Publication History

Publication Date:
31 December 2000 (online)

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1,3,5,8-Tetrathianaphthalene (2, TTN; 1,4,5,8-tetrathiatetralin) has been synthesized in one step from 4,5-bis(benzoylthio)-1,3-dithiole-2-thione (1) and cis-dichloroethylene in high yield. TTN (2) is readily converted into tetrathiafulvalene (2, TTF) upon tetralithiation or bis(ethylenedithio)tetrathiafulvalene (4, BEDT-TTF) upon tetralithiation, sulfur insertion into the carbon-lithium bond pairs and subsequent capping of the reactive intermediate with 1,2-dibromoethane. The rearrangement of TTN allows for a facile synthesis of TTF and a novel non-coupling route to BEDT-TTF.

superconductivity - tetrathianaphthalene - tetrathiafulvalene - bis(ehtylenedithio)tetrathiafulvalene - 13C-NMR