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Diethylaminosulfur trifluoride reacted with cyclic ketoximes bearing substituent(s) that can stabilize a carbocation to cause fluorinative fragmentation, affording fluorinated carbonitrile. Ketoximes lacking such substituents afforded complex mixtures. However, the introduction of a sulfur functionality, which can stabilize a carbocation and can be easily removed from the reaction products, into the ketoxime was effective for producing the fluorinative fragmentation.

Fluorinative Beckmann Fragmentation: Fluorinative .ALPHA.-Cleavage of Cyclic Ketoximes by Diethylaminosulfur Trifluoride.