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; Jieping Zhu

doi:10.1021/ol202554m

Unexpected C-C bond cleavage: synthesis of 1,2,4-oxadiazol-5-ones from amidoximes with pentafluorophenyl or trifluoromethyl anion acting as leaving group

Org Lett. 2011 Dec 2;13(23):6172-5. doi: 10.1021/ol202554m. Epub 2011 Nov 3.

Authors

Thibaud Gerfaud¹, Hai-Long Wei, Luc Neuville, Jieping Zhu

Affiliation

¹ Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.

PMID: 22050220
DOI: 10.1021/ol202554m

Abstract

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.