Beckmann fragmentation
= Beckmann fragmentation
{c}
Fragmentation of an activated <oxime> by cleavage of a carbon–carbon bond anti to its N–O leaving group, yielding a nitrile and a carbon electrophile or a product derived from it. Stabilization of a developing carbocation can favour fragmentation over migration. It differs from the usual <Beckmann rearrangement>, which inserts nitrogen into the migrating carbon–carbon bond and yields an amide after hydrolysis.