Chemistry of Heterocyclic Compounds

, Volume 34, Issue 8, pp 907–911 | Cite as

Synthesis of the precursors of bis(trichloro-1,4-benzoquinonyl)tetrathiafulvalenes

  • G. A. Karlivan
  • R. É. Valter
  • Yu. V. Gulbis


In reaction with potassium butylxanthate and sodium tert-butyltrithionate, 2,5-dihydroxy-3,4,6,7-tetrachloro-2,3-dihydrobenzo[b]furan forms the products from nucleophilic substitution of a chlorine atom, i.e., O-butyl S-(2,5-dihydroxy-4,6,7-trichloro-2,3-dihydrobenzo[b]furan-3-yl) xanthate and S-tert-butyl S′-(2,5-dihydroxy-4,6,7-trichloro-2,3-dihydrobenzo[b]furan-3-yl) trithiocarbonate respectively. Recyclization of the xanthate in concentrated sulfuric acid gave 4-(2,5-dihydroxy-3,4,6-trichlorophenyl)-1,3-dithiol-2-one, which was oxidized by iron trichloride to the corresponding benzoquinone. Cyclization of the trithiocarbonate in the presence of trifluoroacetic and p-toluenesulfonic acid led to 7-hydroxy-5,6,8-trichloro-3a,8b-dithiolo[4,5-b]benzo[d]furan-2-thione.


Iron Potassium Chlorine Sulfuric Acid Benzoquinone 
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Copyright information

© Kluwer Academic/Plenum Publishers 1999

Authors and Affiliations

  • G. A. Karlivan
  • R. É. Valter
  • Yu. V. Gulbis

There are no affiliations available

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