Stereospecific synthesis of dienone iron tricarbonyl complexes by friedelcrafts acylation

https://doi.org/10.1016/S0022-328X(00)82399-2Get rights and content

Abstract

Acylation of diene Fe(CO)3 complexes using the Perrier complexes RCOCl/AlCl3 in methylene chloride at 0°C gives dienone complexes in high yield. Substitution occurs only at unsubstituted terminal carbons of the diene unit. Quenching the reaction mixtures in cold aqueous ammonia gives cis dienone complexes only. Trans dienone complexes are prepared by subsequent isomerization in methanolic sodium methoxide. Formylation of diene Fe(CO)3 complexes proceeds in modest yield using dichloromethylmethyleter/AlCl3 in methylene chloride to give trans-dienal complexes. Reduction of the dienone and dienal complexes as well as those of dienols and dienoic esters with 4 : 1 AlCl3/LiAlH4 results in complete removal of the oxygen function to give trans-diene complexes in good yield.

References (48)

  • R.E. Graf et al.

    J. Organometal. Chem.

    (1973)
  • C.P. Lillya et al.

    J. Organometal. Chem.

    (1971)
  • P. McArdle et al.

    J. Organometal. Chem.

    (1973)
  • R. Pettit et al.

    Adv. in Organometal. Chem.

    (1964)
  • G.G. Ecke, U.S. Patent 3,149,135...
  • D.F. Hunt et al.

    J. Amer. Chem. Soc.

    (1968)
  • D.R. Falkowski et al.

    J. Amer. Chem. Soc.

    (1967)
  • N.A. Clinton et al.

    J. Amer. Chem. Soc.

    (1970)
  • D.A.T. Young et al.

    J. Amer. Chem. Soc.

    (1969)
  • E.O. Greaves et al.

    J. Chem. Soc.

    (1969)
  • N.A. Clinton et al.

    J. Amer. Chem. Soc.

    (1970)
  • D.E. Kuhn et al.

    J. Amer. Chem. Soc.

    (1972)
  • R.E. Graf et al.

    J. Chem. Soc.

    (271)
  • J.E. Mahler et al.

    J. Amer. Chem. Soc.

    (1963)
  • G.F. Emerson et al.

    J. Org. Chem.

    (1964)
  • E.C. Ashley et al.

    J. Amer. Chem. Soc.

    (1966)
  • J.E. Mahler et al.

    J. Amer. Chem. Soc.

    (1963)
  • Cf. Specialist Periodical Reports on Organometallic Chemistry, senior reporters E.W. Abel and F.G.A. Stone, The...
  • B.F.G. Johnson et al.

    J. Chem. Soc.

    (1969)
  • B.F.G. Johnson et al.

    J. Chem. Soc. Dalton

    (1972)
  • B.F.G. Johnson et al.

    J. Chem. Soc.

    (1969)
  • B.F.G. Johnson et al.

    J. Chem. Soc.

    (1971)
  • J.D. Fitzpatrick et al.

    J. Amer. Chem. Soc.

    (1965)
  • G.B. Gill et al.
    (1969)
  • Cited by (0)

    View full text