Synthesis of a chiral monosubstituted derivative of bis(ethylene-dithio)tetrathiafulvalene: Reaction of the cyclic sulfate ester of R,R-1,4-difluorobutane-2,3-diol with 2-thioxo-1,3-dithiole-4,5-dithiolate

Öztürk T., Rice C. R., Wallis J. D.

Journal of Materials Chemistry, vol.5, no.10, pp.1553-1556, 1995 (Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 5 Issue: 10
  • Publication Date: 1995
  • Doi Number: 10.1039/jm9950501553
  • Journal Name: Journal of Materials Chemistry
  • Journal Indexes: Scopus
  • Page Numbers: pp.1553-1556
  • Istanbul Technical University Affiliated: Yes


2-Thioxo-1,3-dithiole-4,5-dithiolate reacts stereospecifically with the cyclic sulfate ester of R,R-1,4-difluorobutane-2,3-diol by two nucleophilic attacks, ring opening of the cyclic sulfate ester at carbon and displacement of the nearer fluorine atom, to form a derivative of the 1,3-dithiolo[4,5-b]-1,4-dithiin ring system. This product is converted in two steps into an analogue of bis(ethylenedithio)tetrathiafulvalene with a 2-fluoro-1-hydroxyethyl side-chain, a new substrate for the preparation of electroactive materials.