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Beckmann Rearrangement; Beckmann Fragmentation

Acid-mediated isomerization of oximes to amides. Oximes of cyclic ketones give ring enlargements:

Beckmann Rearrangement; Beckmann Fragmentation

Certain oximes, particularly those having a quarternary carbon anti to the hydroxyl, are likely to undergo the Beckmann fragmentation to form nitriles instead of amides:

Beckmann Rearrangement; Beckmann Fragmentation

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