Organic Chemistry Portal

Abstracts

Search:

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: jieping.zhuepfl.ch, luc.neuvilleicsn.cnrs-gif.fr

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

DOI: 10.1021/ol202554m (free Supporting Information)


Abstract

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.

see article for more examples



Key Words

N-Heterocycles


ID: J54-Y2011-3430