Unexpected C-C Bond Cleavage: Synthesis of 1,2,4-Oxadiazol-5-ones from Amidoximes with Pentafluorophenyl or Trifluoromethyl Anion Acting as Leaving Group. - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2011

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

Résumé

An unexpected C-C bond cleavage has been observed on pentafluorobenzoylamidoximes under mild basic conditions. This observation has been exploited to develop a new synthesis of 1,2,4-oxadiazol-5-ones from amidoximes using pentafluorobenzoyl chloride or trifluoroacetic anhydride (TFAA) as a double acylating agent. The pentafluorophenyl anion and the trifluoromethyl anion acted as leaving groups in this transformation.

Domaines

Chimie organique
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Dates et versions

hal-00653914 , version 1 (20-12-2011)

Identifiants

Citer

Thibaud Gerfaud, Hai-Long Wei, Luc Neuville, Jieping Zhu. Unexpected C-C Bond Cleavage: Synthesis of 1,2,4-Oxadiazol-5-ones from Amidoximes with Pentafluorophenyl or Trifluoromethyl Anion Acting as Leaving Group.. Organic Letters, 2011, 13 (23), pp.6172-6175. ⟨10.1021/ol202554m⟩. ⟨hal-00653914⟩
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