Beckmann Rearrangement

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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.
McGraw-Hill Dictionary of Scientific & Technical Terms, 6E, Copyright © 2003 by The McGraw-Hill Companies, Inc.
The following article is from The Great Soviet Encyclopedia (1979). It might be outdated or ideologically biased.

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.

The Great Soviet Encyclopedia, 3rd Edition (1970-1979). © 2010 The Gale Group, Inc. All rights reserved.