Beckmann Rearrangement

Beckmann Rearrangement, Mechanism and Applications

In Beckmann rearrangement, conversion of ketoximes to N-substituted amide takes place in presence of acid catalyst (such as- H₂SO₄, SOCl₂, PhSO₂Cl, PCl₅ etc.)
In this rearrangement, migration of a group from carbon to electron deficient nitrogen takes place. The group which is trans to -OH group migrates from carbon atom to nitrogen atom, so the reaction is stereospecific.
Aldoximes, Oxime esters and ethers also undergo this rearrangement.

Mechanism of Beckmann Rearrangement

The following possible mechanism are given below-

Applications of Beckmann Rearrangement

Some uses of Beckmann Rearrangement are given below-
It is used in the production of the monomer unit of Nylon 6 and Nylon 12.
Schmidt reaction also involves Beckmann pathway.
It is mainly used in the synthesis of various steroids and drugs.

Synthesis of Benzonitile

Synthesis of Caprolactam or Nylon-6

Caprolactam is used as raw material in the production of Nylon–6. Caprolactam can be produced by Beckmann rearrangement reaction of cyclohexanone and oxime.

Synthesis of Isoquinoline