Beckmann rearrangement

In chemistry, the Beckmann rearrangement is an acid-catalyzed rearrangement of an oxime to an amide. The oxime is formed by the reaction of a carbonyl with hydroxylamine.

This example reaction starting with cyclohexanone to the caprolactam is the most important application of the Beckmann rearrangement. The caprolactam is hydrolysed and then polymerized to Nylon.

References

• Beckmann, E.; Ber. 1886, 19, 988.
• Donaruma, L. G.; Heldt, W. Z.; Org. React. 1960, 11, 1–156.
• Gawley, R. E.; Org. React. 1988, 35, 1–420.