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Bucherer-Bergs reaction : ウィキペディア英語版 | 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.〔Bucherer, H. T.; Fischbeck, H. T. ''J. Prakt. Chem.'' 1934, ''140'', 69.〕〔Bucherer, H. T.; Steiner, W. ''J. Prakt. Chem.'' 1934, ''140'', 291.〕〔Bergs, H. Ger. pat. 566,094 (1929).〕〔Ware, E. ''Chem. Rev.'' 1950, ''46'', 403. (Review) 〕 The reaction is named after Hans Theodor Bucherer. ''Overall Reaction'' ==Reaction Mechanism==
The addition of KCN to the carbonyl compound gives rise to the cyanohydrin. This is followed by an SN2 reaction with NH3 to form aminonitrile. Nucleophilic addition of aminonitrile to CO2 leads to cyano-carbamic acid, which undergoes an intramolecular ring closing to 5-imino-oxazolidin-2-one. The 5-imino-oxazolidin-2-one rearranges to form the hydantoin product via an isocyanate intermediate.
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