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

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 8-(2,5-dihydroxy-4,6,7-trichloro-2,3-dihydrobenzo[b]furan-3-yl) xanthate and 8-tert-butyl-8′-(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.

How to Cite
Karlivan, G. A.; Valter, R. É.; Gulbis, Y. V. Chem. Heterocycl. Compd. 1998, 34, 907. [Khim. Geterotsikl. Soedin. 1998, 34, 1055.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02311324