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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
Article

Abstract

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.

Keywords

Iron Potassium Chlorine Sulfuric Acid Benzoquinone 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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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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