Download PDF
Synthesis 2003(1): 0124-0128
DOI: 10.1055/s-2003-36258
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Novel Synthesis of Dithieno[2,3-b:3′,2′-d]thiophene and its Bromo Derivatives

Valentine G. Nenajdenko*, Denis V. Gribkov, Viktor V. Sumerin, Elizabeth S. Balenkova
Department of Chemistry, Moscow State University, 119899 Moscow, Russia
Fax: +7(95)9328846; e-Mail: Nen@acylium.chem.msu.su;
Further Information

Publication History

Received 18 October 2002
Publication Date:
18 December 2002 (online)

    Permissions and Reprints All articles of this category

Abstract

Two new approaches to multigram synthesis of dithieno[2,3-b:3′,2′-d]thiophene are described. Various mono-, di-, tri- and tetrabromides of dithieno[2,3-b:3′,2′-d]thiophene are prepared in good yield.

Key words

thiophenes - sulfur - heterocycles - bromine - electrophilic aromatic substitutions

    References

  • 1 Kiani MS. Mitchell GR. Synth. Met.  1992,  46:  293 
    CrossrefGoogle Scholar
  • 2a Morrison JJ. Murray MM. Li XC. Holmes AB. Morratti SC. Friend RH. Sirringhaus H. Synth. Met.  1999,  102:  987 
    CrossrefGoogle Scholar
  • 2b Li XC. Sirringhaus H. Garnier F. Holmes AB. Morratti SC. Feeder N. Clegg W. Teat SJ. Friend RH. J. Am. Chem. Soc.  1998,  120:  2206 
    CrossrefGoogle Scholar
  • 3 Halls JJM. Walsh CA. Greenham NC. Marseglia EA. Friend RH. Moratti SC. Holmes AB. Nature (London)  1995,  376:  498 
    CrossrefGoogle Scholar
  • 4 Greenham NC. Moratti SC. Bradley DDC. Friend RH. Holmes AB. Nature (London)  1993,  365:  628 
    CrossrefGoogle Scholar
  • 5 Pandya LJ. Tilak BD. Chem. Ind. (London, U.K.)  1958,  981 
    Google Scholar
  • 6 Jong F. Janssen MJ. J. Org. Chem.  1971,  36:  1998 
    Google Scholar
  • 7 Kabir SMH. Miura M. Sasaki S. Harada G. Kuwatani Y. Yoshida M. Iyoda M. Heterocycles  2000,  52:  761 
    Google Scholar
  • 8 Iyoda M. Miura M. Sasiki S. Kabir SMH. Kuwatani Y. Yoshida M. Tetrahedron Lett.  1997,  38:  4581 
    CrossrefGoogle Scholar
  • 9 Jong F. Janssen MJ. J. Org. Chem.  1971,  36:  1645 
    CrossrefGoogle Scholar
  • 10 Kellogg RM. Schaap AP. Wynberg H. J. Org. Chem.  1969,  34:  343 
    Google Scholar
  • 11 Fournari P. Meunier P. Bull. Soc. Chim. Fr.  1974,  3-4:  583 
    Google Scholar
  • 12 Archer WJ. Taulor R. J. Chem. Soc., Perkin Trans 2  1982,  301 
    CrossrefGoogle Scholar
  • 13 Wynberg H. Bantjes A. J. Org. Chem.  1959,  24:  1421 
    Google Scholar
  • 14 Rajca A. Wang H. Pink M. Rajca S. Angew. Chem. Int. Ed.  2000,  39:  4481 
    CrossrefGoogle Scholar