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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 25, 1995 - Issue 5
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Original Articles

The Boekelheide Reaction: Trifluoroacetic Anhydride as a Convenient Acylating Agent

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Pages 629-633 | Received 31 Aug 1994, Published online: 23 Sep 2006

References

  • Katada , M. 1947 . J. Pharm. Soc. Jpn. , 67 : 51
  • Boekelheide , V. and Linn , W. J. 1954 . J. Am. Chem. Soc. , 76 : 1286
  • Cohen , T. and Deets , G. L. 1972 . J. Am. Chem. Soc. , 94 : 932
  • Katritsky , A. R. 1971 . Chemistry of the Heterocyclic N-oxides. , 353 Academic Press .
  • Oae , S. , Tamagaki , S. , Negoro , T. , Ogino , K. and Kozuka , S. 1968 . Tetrahedron Letters , : 917
  • Oae , S. , Tamagaki , S. , Negoro , T. and Kozuka , S. 1970 . Tetrahedron , 26 : 4051
  • Kozuka , S. , Tamagaki , S. , Negoro , T. and Oae , S. 1968 . Tetrahedron Letters , : 923
  • Bodalski , R. and Katritsky , A. R. 1968 . Tetrahedron Letters , : 257
  • Tamagaki , S. , Kozuka , S. and Oae , S. 1968 . Tetrahedron Letters , : 4765
  • Koenig , T. 1966 . J. Am. Chem. Soc. , 88 : 4045
  • Korytnyk , W. , Srivastava , S. C. , Angelino , N. , Potti , P. G.G. and Paul , B. 1973 . J. Med. Chem. , 16 : 1096
  • Kozuka , S. , Tamagaki , S. , Negoro , T. and Oae , S. 1968 . Tetrahedron Letters , : 923
  • McKillop , A. and Bhagrath , M. K. 1985 . Heterocycles , 23 : 1697
  • In fact, trifluoroacetic anhydride was once used for the Boekelheide reaction (see ref 4.) in the syntheses of some pyridoxal derivatives. This method was not extended to other substrates. Thus it is not known as a general procedure.
  • Unpublished results.
  • Bell , T. W. , Cho , Y.-M. , Firestone , A. , Healy , K. , Liu , J. J. , Ludwig , R. and Rothenberger , S. D. 1990 . Org. Syntheses , 69 : 226
  • Nicolaou , K. C. , Maligres , P. , Suzuki , T. , Wendeborn , S. V. , Dai , W.-M. and Chadha , R. K. 1992 . J. Am. Chem. Soc. , 114 : 8890

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