Elsevier

Tetrahedron Letters

Volume 34, Issue 23, 4 June 1993, Pages 3683-3686
Tetrahedron Letters

Synthesis of symmetrical diaryl 1,2-diketones from grignard reagents and 1,1′-Oxalylimidazole

https://doi.org/10.1016/S0040-4039(00)79200-8Get rights and content

Abstract

Symmetrical diaryl 1,2-diketones (α-diketones) are obtained in reasonably good yields when readily accessible 1,1′-oxalylimidazole is treated with two equivalents of an aryl Grignard reagent.

Reaction of two equivalents of aryl Grignard with 1,1′-oxalyldiimidazole yields diaryl-1,2-diketones (benzils) in 55–80% yield, even for relatively sterically hindered examples.

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References (24)

  • D. Lenoir

    Synthesis

    (1989)
  • R.H. Mitchell et al.

    Tetrahedron Lett.

    (1986)
  • H.A. Staab

    Angew. Chem., Int. Ed. Engl.

    (1962)
  • A.J. WaringT. LairdE.S. Krongauz

    Russ. Chem. Rev.

    (1977)
    D. Seyferth et al.

    J. Org. Chem.

    (1991)
  • J. Kollonitsch

    J. Chem. Soc. A

    (1966)
  • M.P. Sibi et al.

    Tetrahedron Lett.

    (1992)
  • U.T. Mueller-Westerhoff et al.

    Tetrahedron Lett.

    (1993)
  • T. LairdT. Laird
  • H.A. Staab et al.

    Liebigs Ann. Chem.

    (1962)
  • M. Araki et al.

    Bull. Chem. Soc. Jpn

    (1974)
  • T. Sakan et al.

    Chem. Lett.

    (1972)
  • S. Murata

    Chem. Lett.

    (1983)
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