View PDF Version
 
DOI: 10.1039/A707033K (Paper) Reference Section for: Chem. Commun., 1997, 2355-2356

Synthesis of polyfunctionalized thiophenes and enediynes via ring-opening reactions of 3-lithiated thieno[2,3-b](and [3,2-b])thiophenes, 3,4-dilithiated thieno[2,3-b]thiophenes and 3,6-dilithiated thieno[3,2-b]thiophenes

(Note: The full text of this document is currently only available in the PDF Version )

Lance S. Fuller, Brian Iddon MP and Kevin A. Smith

Abstract

Solutions of the title lithiated thienothiophenes were synthesized from 2,5-disubstituted 3,4-dibromothieno[2,3-b]thiophenes or 3,6-dibromothieno[3,2-b]thiophenes via Br → Li exchange with 1.0 or 2.0 equiv. of BuLi (THF, –78 °C), respectively, and gave either polyfunctionalized thiophenes or polyfunctionalized enediynes (by a novel tandem ring-opening process in these cases) on being allowed to warm up to ambient temperature.

References

  1. R. P. Dickinson and B. Iddon, Tetrahedron Lett., 1970, 975 CrossRef CAS; Int. J. Sulfur Chem. C, 1971, 6, 59 Search PubMed; J. Chem. Soc. C, 1971, 3447 Search PubMed.
  2. B. Iddon, Heterocycles, 1983, 20, 1127 CAS.
  3. R. M. Scrowston, Adv. Heterocycl. Chem., 1981, 29, 171 CAS.
  4. R. P. Dickinson and B. Iddon, J. Chem. Soc. C, 1970, 2592 RSC; 1971, 182; 1971, 2504.
  5. S. Gronowitz and T. Frejd, Acta Chem. Scand., 1969, 23, 2540 CAS.
  6. S. Gronowitz, Adv. Heterocycl. Chem., 1963, 1, 1 CAS (see p. 75).
  7. S. Gronowitz and T. Frejd, Chem. Heterocycl. Compds. (Engl. Transl.), 1978, 14, 353 Search PubMed.
  8. S. Gronowitz, Chem. Heterocycl. Compds. (Engl. Transl.), 1994, 30, 1252 Search PubMed.
  9. T. Frejd, Chem. Heterocycl. Compds., 1992, 44, 257 Search PubMed; Thiophene and Its Derivatives, ed. S. Gronowitz, Wiley-Interscience, New York, 1992, part 5, ch. II, p. 257(in particular see p. 721) Search PubMed.
  10. P. Moses and S. Gronowitz, Arkiv. Kemi, 1962, 18, 119 Search PubMed.
  11. S. Gronowitz, Phosphorus, Sulfur, Silicon Relat. Elem., 1993, 74, 113 CAS.
  12. S. Gronowitz, A.-B. Hörnfeldt, E. Lukevics and O. Pudova, Synthesis, 1994, 40 CrossRef CAS.
  13. e.g. see Modern Acetylene Chemistry, ed. P. J. Stang and F. Diederich, VCH, Weinheim, 1995 Search PubMed.
  14. L. S. Fuller, B. Iddon and K. A. Smith, J. Chem. Soc., Perkin Trans. 1, 1997, in the press Search PubMed.
  15. K. Yui, H. Ishida, Y. Aso, T. Otsubo, F. Ogura, A. Kawamoto and J. Tanaka, Bull. Chem. Soc. Jpn., 1989, 62, 1547 CAS.
  16. T. Otsubo, Y. Kono, N. Hozo, H. Miyamoto, Y. Aso, F. Ogura, T. Tanaka and M. Sawada, Bull. Chem. Soc. Jpn., 1993, 66, 2033 CAS.
Click here to see how this site uses Cookies. View our privacy policy here.