BUCHERER REACTION PDF

The Bucherer reaction in organic chemistry is the reversible conversion of a naphthol to a naphthylamine in the presence of ammonia and sodium bisulfite. The reaction is widely used in the synthesis of dye precursors aminonaphthalenesulfonic acids. The German chemist Hans Theodor Bucherer — discovered independent from Lepetit its reversibility and its potential especially in industrial chemistry. Bucherer published his results in and his name is connected to this reaction. The organic reaction also goes by the name Bucherer-Lepetit reaction or wrongly the Bucherer-Le Petit reaction.

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The Bucherer reaction in organic chemistry is the reversible conversion of a naphthol to a naphthylamine in the presence of ammonia and sodium bisulfite. The German chemist Hans Theodor Bucherer — discovered independent from Lepetit its reversibility and its potential especially in industrial chemistry. Bucherer published his results in and his name is connected to this reaction. The organic reaction also goes by the name Bucherer-Lepetit reaction or wrongly the Bucherer-Le Petit reaction.

The reaction is used to convert 1,7-dihydroxynaphthalene into 7-aminonaphthol and 1-aminonaphthalenesulfonic acid into 1-hydroxynaphthalenesulfonic acid. It is also useful for transamination reactions of 2-aminonaphthalenes.

This leads to resonance stabilized adducts 1a-1e. In the next step a bisulfite anion adds to C3 through 1e. This results in the formation of 3a which tautomerizes to the more stable 3b to the sulfonic acid of tetralone. A nucleophilic addition follows of the amine with formation of 4a and its tautomer 4b loses water to form the resonance stabilized cation 5a. This compound is deprotonated to the imine 5b or the enamine 5c but an equilibrium exists between both species.

The enamine eliminates sodium bisulfite with formation of naphthylamine 6. It is important to stress that this is a reversible reaction.

Bucherer

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Bucherer–Bergs reaction

Mauktilar This page was last edited on 8 Marchat Nucleophilic addition of aminonitrile to CO 2 leads to cyano-carbamic acid, which undergoes an intramolecular ring closing to 5-imino-oxazolidinone. One limitation of the Bucherer—Bergs reactions is that it only has one point of diversity. With this solvent, aldehydes reacted well, and ketones gave excellent yields. In the past, the Bucherer—Bergs reaction bersg had problems with polymerization, long reaction time, and difficult work-up.

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Bucherer reaction

Reaction Mechanism[ edit ] Reaction mechanism for the Bucherer—Bergs reaction 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 CO2 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. In , Bergs issued a patent that described his own synthesis of a number of 5-substituted hydantoins. Bucherer and Steiner also found that cyanohydrins would react just as well as carbonyl compounds to produce hydantoins. With this solvent, aldehydes reacted well, and ketones gave excellent yields.

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Bucherer-Bergs Reaction

Last updated December 23, The Bucherer reaction in organic chemistry is the reversible conversion of a naphthol to a naphthylamine in the presence of ammonia and sodium bisulfite. The German chemist Hans Theodor Bucherer — discovered independent from Lepetit its reversibility and its potential especially in industrial chemistry. Bucherer published his results in and his name is connected to this reaction. The organic reaction also goes by the name Bucherer-Lepetit reaction or wrongly the Bucherer-Le Petit reaction.

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Reaction Details

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