View PDF Version
 
DOI: 10.1039/A702167D (Paper) Reference Section for: J. Chem. Res. (S), 1997, 402-403

Direct Synthesis of trans-1,4-Diacetoxycyclohexa-2,5-diene by Electrochemical Reduction of r-1,t-4-Diacetoxy-t-2,c-3-dibromocyclohex-5-ene

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

Latif Kelebekli, Ümit Demir and Yunus Kara

Abstract

Electrochemical reduction of r-1,t-4-diacetoxy-t-2,c-3-dibromocyclohex-5-ene 1 gives only trans-1,4-diacetoxycyclohexa-2,5-diene 2 in good yield while the commonly used Zn reduction gives a product mixture containing 2 and acetoxybenzene 3 derived from acetoxy elimination.

References

  1. H. Yagi, D. M. Jerina, G. J. Kasperek and T. C. Bruice, Proc. Natl. Acad. Sci. USA, 1985, 69, 1972 Search PubMed.
  2. A. Fischer and G. N. Henderson, Tetrahedron Lett., 1980, 21, 701 Search PubMed.
  3. M. Balci, Y. Sütbeyaz and H. Seçen, Tetrahedron, 1990, 46, 3715 Search PubMed.
  4. T. Posternak, The Cyclitols, Hermann, Paris, 1st edn., 1965 Search PubMed.
  5. (a) G. Legler and M. Herrchen, FEBS Lett., 1981, 135, 139 Search PubMed; (b) A. P. Kozikowski, A. H. Fauq, G. Powis, P. Kurian and F. T. Crews, J. Chem. Soc., Chem. Commun., 1992, 362 Search PubMed.
  6. D. E. Worral and S. Cohen, J. Am. Chem. Soc., 1936, 58, 533 Search PubMed.
  7. H. M. Crawford and M. McDonald, J. Am. Chem. Soc., 1949, 71, 2681 Search PubMed.
  8. Z. Florjanczyk, W. Kuran, S. Pasynkiewicz and G. Kwas, J. Organomet. Chem., 1976, 112, 21 Search PubMed.
  9. F. Alonso and M. Yus, Tetrahedron, 1991, 47, 7471 Search PubMed.
  10. (a) J. March, Advanced Organic Chemistry, Wiley, New York, 4th edn., 1992, p. 912 Search PubMed; (b) H. W. Moore, K. F. West, K. Chow, M. Fernandez and N. V. Nguyen, J. Org. Chem., 1987, 52, 2537 Search PubMed; (c) J. S. Cha and H. C. Brown, J. Org. Chem., 1993, 58, 3979 Search PubMed.
  11. J. March, Advanced Organic Chemistry, Wiley, New York, 4th. edn., 1992, p. 1034 Search PubMed.
  12. H. Seçen, A. Maras, Y. Sütbeyaz and M. Balci, Synth. Commun., 1992, 22, 2613 Search PubMed.
  13. F. Barba, A. Guirado and I. Barba, J. Org. Chem., 1984, 49, 3022 Search PubMed.
  14. K. M. O'Connel and D. H. Evans, J. Am. Chem. Soc., 1983, 105, 1473 Search PubMed.
  15. H. O. House and R. S. Ro, J. Am. Chem. Soc., 1958, 80, 182 Search PubMed.
  16. F. Alonso, I. Barba and M. Yus, Tetrahedron, 1990, 46, 2069 Search PubMed.
  17. P. M. Hudnall and D. R. Rieke, J. Am. Chem. Soc., 1973, 95, 2646 Search PubMed.
  18. C. Casanova and R. H. Rogers, J. Org. Chem., 1974, 39, 2408 Search PubMed.