Bucherer-Bergs Hydantoin Synthesis. 17 May, / by SK / in Reactions. Overall Score4. Generality. Reagent Availability. Experimental User Friendliness . The Bucherer-Bergs reaction is the chemical reaction of carbonyl compounds (or cyanohydrins) with ammonium carbonate and potassium cyanide to give. The Formation of Hydantoin from Carbonyl Compound with Potassium Cyanide and Ammonium Carbonate is Referred to as the Bucherer-bergs Reaction.
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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. Compared with reports in the literature, this makes so the reaction can be carried out at a lower temperature, have a shorter reaction time, a higher yield, and a more simple work-up. Bucherer and Steiner also found that cyanohydrins would react just as well as carbonyl compounds to produce buucherer.
In Bucherer and Steiner proposed a mechanism for the reaction. First, the reaction of 2-Methyleneaziridine 1 with Grignard reagentcatalytic Cu Iand R 2 -X causes the 2-Methyleneaziridine to ring open and form a ketimine 2. However, in other cases, there is no selectivity at all, resulting in a 1: With this solvent, aldehydes reacted well, bucherfr ketones gave excellent yields.
Heterocyclic ChemistryHoboken, New Jersey: Retrieved from ” https: The hydantoins formed by the Bucherer—Bergs reaction have many useful applications.
Bucherer and Steiner also found that cyanohydrins would react just as well as carbonyl compounds to produce hydantoins.
All articles with unsourced statements Articles with unsourced statements from July Tetrahedron Letters47 Following condensation of the carbonyl with the ammonium, the formed imine is attacked by the isocyanide to form the aminonitrile. 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.
With this solvent, aldehydes reacted well, and ketones gave excellent yields. Heterocyclic ChemistryHoboken, New Jersey: One way to rraction the number of points of diversity is by combining a reaction with 2-Methyleneaziridine with the Bucherer—Bergs reaction in a one-pot synthesis see Figure 1. The 5-imino-oxazolidinone rearranges to form the hydantoin product via an isocyanate intermediate.
This is followed by an S N 2 reaction with NH 3 to form aminonitrile. However, in other cases, there is no selectivity at all, resulting in a 1: Ultrasonics Sonochemistry3SS One limitation of the Bucherer—Bergs reactions is that it only has one point of diversity.
Nucleophilic addition of aminonitrile to CO 2 leads to cyano-carbamic acid, which undergoes an intramolecular ring closing to 5-imino-oxazolidinone. More recently, many organic reactions have been accelerated by ultrasonic irradiation.
Bucherer Bergs Reaction
Views Read Edit View history. One improvement on the Bucherer—Bergs reaction has been the use of ultrasonication. This reaction has three points of chemical diversity as the structure of the aziridine starting compound, the organometallic reagent, and the electrophile can all be varied to synthesize a different hydantoin. While the end product of the Bucherer—Bergs reaction is a hydantointhe hydantoin can undergo hydrolysis to form an aminio acid.
One way to increase the number of points of diversity is by combining a reaction with 2-Methyleneaziridine with the Bucherer—Bergs reaction in a one-pot synthesis see Figure 1. From Wikipedia, the free encyclopedia. In other projects Wikimedia Commons. While there were some issues with the mechanism, it was mostly accurate.
In some cases, the carbonyl starting material can be sufficiently sterically biased so a single stereoisomer is observed.
One limitation of the Bucherer—Bergs reactions is that it only has one point of diversity. The addition of KCN to the carbonyl compound gives rise to the cyanohydrin.
Bucherer-Bergs Reaction
Only changes in the structure of the starting ketone or aldehyde will lead to variations in the final hydantoin. This page was last edited on 8 Marchat First, the reaction of 2-Methyleneaziridine 1 with Grignard reagentcatalytic Cu Bufhererand R 2 -X causes the 2-Methyleneaziridine to ring open and form a ketimine 2.
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. The 5-imino-oxazolidinone rearranges to form the hydantoin product via an isocyanate intermediate.
►Bucherer-Bergs reaction –
Carbon-carbon bond forming reactions Condensation reactions Heterocycle forming reactions Multiple component reactions Name reactions Nitrogen heterocycle forming reactions. An example taken from “Name Reactions: Reactions similar to the Bucherer—Bergs reaction were first seen in gucherer 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.
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.