Beckmann Rearrangement

Also found in: Wikipedia.

Beckmann rearrangement

[′bek·män rē·ə′rānj·mənt]
(organic chemistry)
An intramolecular change of a ketoxime into its isomeric amide when treated with phosphorus pentachloride.

Beckmann Rearrangement


a chemical reaction that converts oximes into acid amides under the influence of acidic dehydrating agents (PCl5, H2SO4, oleum, and others):

where R and R’ are identical or different organic radicals (CH3, C2H5, C6H5, and so on). The Beckmann rearrangement is used in industry to obtain kapron (a stage in the conversion of cyclohexanon oxime into ∊-caprolactam). The Beckmann rearrangement was discovered in 1886 by the German chemist E. O. Beckmann.