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.


Published in:
Organic Letters, 13, 23, 6172-6175
Year:
2011
ISSN:
1523-7052
Keywords:
Laboratories:




 Record created 2011-12-05, last modified 2018-03-17


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