Polyhalogenoaromatic compounds. Part XII. Synthesis and cycloaddition reactions of pentafluoro- and pentachloro-benzonitrile N-oxide

Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39700001165

Abstract

Pentafluoro- and pentachloro-benzonitrile N-oxide were prepared from the corresponding pentahalogenobenzaldehyde oximes. The fluoro-compound dimerised to 3,4-bis(pentafluorophenyl)furoxan, whereas the chlorocompound was stable. Both the nitrile oxides readily underwent cycloadditions with styrene and phenylacetylene, to give the appropriate 3-pentahalogenophenyl-5-phenyl-isoxazolines and -isoxazoles.

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