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Stereospecific Synthesis of 2,4-Dienoci Acid Derivatives from Vinylmercuric Chlorides and Acrylic Acid Derivatives by Palladium(II) Salt

  • Kim Jin Il (Department of Industrial Chemistry, Hanyang University) ;
  • Lee Jong Tae (Department of Industrial Chemistry, Hanyang University)
  • Published : 1986.12.20

Abstract

The reaction of (E)- or (Z)-1-alkenylmercuric chlorides with acrylic acid derivatives in the presence of 10 mol% of lithium trichloropalladate ($LiPdCl_3$) and an equimolar amount of cupric chloride, as a reoxidant for the palladium, in acetonitrile at room temperature gave the corresponding (E,E)- or (E,Z)-2,4-dienoic acid derivatives stereospecifically in moderate to good yields. The reaction of (E)- or (Z)-3-chloromercuripropenoic acid with olefins under the reaction condintion described above similarly gave good yields of (E,E)- or (Z,E)-2,4-dienoic acids stereospecifically. A side reaction, the homocoupling of alkenylmercuric chlorides, could be minimized by employing the condition described above. However, in the reaction of 3-chloromercuripropenoic acid with olefins under the present condition, the homocoupled side reaction product was not produced.

Keywords

References

  1. J. Org. Chem. v.40 H.A. Dieck;R.F. Heck
  2. J. Org. Chem. v.43 B.A. Patel;J.E. Dickerson;R.F. Heck
  3. J. Org. Chem. v.46 J.I. Kim;B.A. Patel;R.F. Heck
  4. J. Org. Chem. v.46 B.A. Patel;J.I. Kim;D.D. Bender;L.C. Kao;R.F. Heck
  5. J. Org. Chem. v.48 W. Fischetti;K.T. Mak;F.G. Stakem;J.I. Kim;A.L. Rheingold;R.F. Heck
  6. Bull. Korean Chem. Soc. v.6 J.I. Kim;J.T. Lee;K.D. Yeo
  7. Bull. Korean Chem. Soc. v.7 J.I. Kim;J.T. Lee
  8. Bull. Korean Chem. Soc. v.7 J.I. Kim;J.T. Lee;C.K. Choi
  9. J. Am. Chem. Soc. v.90 R.F. Heck
  10. J. Org. Chem. v.41 R.C. Larock
  11. J. Organometal. Chem. D. Seyferth;L. Vaughan;R. Suzuki
  12. J. Am. Chem. Soc. v.97 H.C. Brown;S.K. Gupta
  13. J. Am. Chem. Soc. v.60 M.R. Kharrasch;R.C. Seyler;F.R. Mayo
  14. J. Org. Chem. v.49 P.J. Harrington;L.S. Hegedus
  15. J. Am. Chem. Soc. v.94 R.C. Larock;S.K. Gupta;H.C. Brown
  16. J. Org. Chem. v.24 W.P. Norris
  17. J. Org. Chem. v.45 J.R. Weir;B.A. Patel;R.F. Heck
  18. J. Org. Chem. v.37 R.F. Heck;J.P. Nolley
  19. Tetrahedron v.25 G. Kresze;J. Firl;H. Braun
  20. Org. Synth. v.40 R.N. Mcdonald;T.W. Campbell
  21. J. Org. Chem. v.36 F.J. Villani;C.A. Fllis;M.D. Yudis;J.B. Morton
  22. Synthesis A. Loupy;K. Sogadji;J. Seyden-Penne
  23. Bull. Soc. Chim. France G. Sturtz
  24. Synthesis M. Kluba;A. Zwierzak
  25. J. Chem. Soc. Elvidge
  26. J. Am. Chem. Soc. v.96 H.A. Dieck;R.F. Heck
  27. J. Org. Chem. v.47 S. Tsuboi;T. Masuda;A. Takeda
  28. J. Chem. Soc. Chem. Commun. Y.S. Rao