Unexpected C–C Bond Cleavage: Synthesis of 1,2,4-Oxadiazol-5-ones from Amidoximes with Pentafluorophenyl or Trifluoromethyl Anion Acting as Leaving Group
An unexpected C-C bond cleavage has been observed on pentafluorobenzoylamidoxlmes 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.
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Gerfaud, T., Wei, H.-L., Neuville, L., & Zhu, J. (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. Organic Letters, 13(23), 6172–6175. https://doi.org/10.1021/ol202554m
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WOS:000297274700010
2011
13
23
6172
6175
NON-REVIEWED
EPFL