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Unexpected C-C Bond Cleavage: Synthesis of 1,2,4-Oxadiazol-5-ones from Amidoximes with Pentafluorophenyl or Trifluoromethyl Anion Acting as Leaving Group

Thibaud Gerfaud, Hai-Long Wei, Luc Neuville* and Jieping Zhu*

*Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France, Email:,

T. Gerfaud, H.-L. Wei, L. Neuville, J. Zhu, Org. Lett., 2011, 13, 6172-6175.

DOI: 10.1021/ol202554m


Pentafluorophenyl anion and trifluoromethyl anion as leaving groups enable a new synthesis of 1,2,4-oxadiazol-5-ones from amidoximes using pentafluorobenzoyl chloride or trifluoroacetic anhydride (TFAA) as a double acylating agent.

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ID: J54-Y2011-3430