O-Cyanoisocyanates

Under Beckmann rearrangement conditions, O-tosyl oximes furnish the cyanoanilines, while the parent oxime gives the intermediate 2-cyanophenylisocyanate220. When the O-acetyl oximes are reacted with sodium azide, cyanoanilines are also produced. Campbell proposed a mechanism where the E-isomer of the oxime suffers elimination, forming a 2-cyanoisocyanate, which upon hydrolysis and decarboxylation gives 2-cyanoani line (Scheme... 

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