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Bucherer–Bergs reaction

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Bucherer-Bergs reaction

The Bucherer—Bergs reaction is the chemical reaction of carbonyl compounds aldehydes or ketones or cyanohydrins with ammonium carbonate and potassium cyanide to give hydantoins. Following condensation of the carbonyl with the ammonium, the formed imine is attacked by the isocyanide to form the aminonitrile. Nucleophilic addition of aminonitrile to CO 2 leads to cyano-carbamic acid, which undergoes an intramolecular ring closing to 5-imino-oxazolidinone. The 5-imino-oxazolidinone rearranges to form the hydantoin product via an isocyanate intermediate. Reactions similar to the Bucherer—Bergs reaction were first seen in and by Ciamician and Silber, who obtained 5,5-dimethylhydantoin from a mixture of acetone and hydrocyanic acid after it had been exposed to sunlight for five to seven months.


Continuous Synthesis of Hydantoins: Intensifying the Bucherer–Bergs Reaction


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