Beckmann Rearrangement
An acid-induced rearrangement of oximes to give amides.
This reaction is related to the Hofmann and Schmidt Reactions and the Curtius Rearrangement, in that an electropositive nitrogen is formed that initiates an alkyl migration.
Mechanism of the Beckmann Rearrangement
Oximes generally have a high barrier to inversion, and accordingly this reaction is envisioned to proceed by protonation of the oxime hydroxyl, followed by migration of the alkyl substituent "trans" to nitrogen. The N-O bond is simultaneously cleaved with the expulsion of water, so that formation of a free nitrene is avoided.
Recent Literature
he Beckmann Rearrangement Executed by Visible-Light-Driven Generation of Vilsmeier-Haack Reagent
Dichloroimidazolidinedione-Activated Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
Scope and Mechanism of a True Organocatalytic Beckmann Rearrangement with a Boronic Acid/Perfluoropinacol System under Ambient Conditions
Beckmann Rearrangement of Ketoximes to Lactams by Triphosphazene Catalyst
Efficient Iodine-Mediated Beckmann Rearrangement of Ketoximes to Amides under Mild Neutral Conditions
Beckmann Rearrangement of Oximes under Very Mild Conditions
Bromodimethylsulfonium Bromide-ZnCl2: A Mild and Efficient Catalytic System for Beckmann Rearrangement
Hypervalent Iodine-Mediated Beckmann Rearrangement of Ketoximes
Au/Ag-Cocatalyzed Aldoximes to Amides Rearrangement under Solvent- and Acid-Free Conditions
Beckmann reaction of oximes catalysed by chloral: mild and neutral procedures
Mercury-Catalyzed Rearrangement of Ketoximes into Amides and Lactams in Acetonitrile
Direct and Catalytic Amide Synthesis from Ketones via Transoximation and Beckmann Rearrangement under Mild Conditions
Deacetylative Amination of Acetyl Arenes and Alkanes with C-C Bond Cleavage
Solvent-Free and One-Step Beckmann Rearrangement of Ketones and Aldehydes by Zinc Oxide
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