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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 19, 1989 - Issue 9-10
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Original Articles

A Practical Catalytic Procedure for Oxidation of Alcohols Into Aldehydes or Ketones with RuCl3/Water and Ca(OCl)2 or NaIO4

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Pages 1721-1726 | Received 09 Jan 1989, Published online: 24 Oct 2006

References

  • Mys , W. J. and De Jonge , C. R. H. 1986 . Organic Synthesis by oxidation with metal compounds , N.Y. : Plenum Press .
  • Sheldon , R. A. and Kochi , J. K. 1981 . Metal—Catalyzed oxidation of Organic Compounds , N.Y. : Academic Press .
  • Sheldon , R. A. 1985 . Bull. Soc. Chim. Belg. , 94 : 651 For a pertinent review see:
  • Gore , E. S. 1983 . Platinum Metal Review , 27 : 111 Review:
  • Balavoine , G. , Eskenazi , C. , Meunier , F. and Rivière , H. 1984 . Tetrahedron Lett. , 25 : 3187
  • Wolfe , S. , Hasan , S. K. and Campbell , J. R. 1970 . J. Chem. Soc. Chem. Comm. , : 1420
  • Schröder , M. and Griffith , W. P. 1979 . ibid. , : 58
  • Caputo , J. A. and Fuchs , R. 1967 . Tetrahedron Lett. , : 4729
  • Muller , P. and Godoy , J. 1981 . Tetrahedron Lett. , 22 : 2361
  • Matsumoto , M. and Ito , S. 1981 . J. Chem. Soc. Chem. Comm. , : 907
  • Matsumoto , M. and Watanabe , N. 1984 . J. Org. Chem. , 49 : 3435
  • Bilgrien , C. , Davis , S. and Drago , R. S. 1987 . J. Amer. Chem. Soc. , 109 : 3786
  • Sharpless , K. B. , Akashi , K. and Oshima , K. 1976 . Tetrahedron Lett. , : 2503
  • Griffith , W. P. , Ley , S. V. , Whitcombe , P. and White , A. D. 1987 . J. Chem. Soc. Chem. Comm. , : 1625
  • These α, β-acetylenic alcohols were prepared by DIBAL reduction of the corresponding α, β-acetylenic ketones. We thank Dr. Cahiez, G. (Université P. et M. Curie) for generous gifts of these latter materials for their preparation see: Laboue, B. Thèse de l'Université P. et M. Curie, Déc. 1987.
  • Webster , F. X. , Rivas-Enterrios , J. and Silverstein , R. M. 1987 . J. Org. Chem. , 52 : 689
  • Some loss of material was observed during flash chromatography. The crude material were usually high: 85–90% yield of the corresponding aldehyde of ketone.
  • Giddings , S. and Mills , A. 1988 . J. Org. Chem. , 53 : 1103 For a recent study on the optimization of oxidation of 2 - octanol with a biphasic system using NaBrO3/RuCl3, see

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