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Encyclopedia > Beckmann rearrangement


In chemistry, the Beckmann rearrangement is the rearrangement of a ketoxime to the corresponding amide in concentrated sulfuric acid, phosphorus pentachloride or a few other catalysts. The oxime is formed by the reaction of a ketone with hydroxylamine.


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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.




  Results from FactBites:
 
Rearrangement (7059 words)
Rearrangements consisting of consecutive 1,2-shifts often take place in a concerted, and therefore stereospecific fashion; however, it must not be assumed that the group shifts are simultaneous.
Rearrangement to a 2º-carbocation is favored by relief of small-ring strain in the case of pinene, and relief of steric congestion in the case of camphene.
The rearrangement of acyl nitrenes to isocyanates that is the crux of the Hofmann, Curtius and Lossen rearrangements, is paralleled by the rearrangement of acyl carbenes to ketenes, a transformation called the Wolff rearrangement.
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