Bucherer–Bergs Reaction
   HOME
*



picture info

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. The reaction is named after Hans Theodor Bucherer. ''Overall Reaction'' Reaction Mechanism 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-oxazolidin-2-one. The 5-imino-oxazolidin-2-one rearranges to form the hydantoin product via an isocyanate intermediate. History Reactions similar to the Bucherer–Bergs reaction were first seen in 1905 and 1914 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. In 1929, Bergs issued a patent that described his own synthesis of a ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  




Hans Theodor Bucherer
Hans Theodor Bucherer (19 May 1869 – 29 May 1949) was a German chemist and gave name to several chemical reactions, for example the Bucherer carbazole synthesis, the Bucherer reaction, and the Bucherer–Bergs reaction Life Bucherer started studying chemistry at the University of Munich, University of Karlsruhe and later with Johannes Wislicenus at the University of Leipzig. After he received his Ph.D in 1893 he worked at BASF. He became professor at Technical University of Dresden in 1901 changed to the Technical University of Berlin in 1913 and became professor at the Technical University of Munich The Technical University of Munich (TUM or TU Munich; german: Technische Universität München) is a public research university in Munich, Germany. It specializes in engineering, technology, medicine, and applied and natural sciences. Establis ... in 1926. References 1869 births 1949 deaths 20th-century German chemists Academic staff of the Technical University o ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are common and play important roles in the technology and biological spheres. Structure and bonding Aldehydes feature a carbon center that is connected by a double bond to oxygen and a single bond to hydrogen and single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp2- hybridized. The aldehyde group is somewhat polar. The C=O bond length is about 120-122 picometers. Physical properties and characterization Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes are more soluble in water, formaldehyde and acetaldehyde completely so. The volatile aldehydes have pungent odors. Al ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Stereoisomer
In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in space. This contrasts with structural isomers, which share the same molecular formula, but the bond connections or their order differs. By definition, molecules that are stereoisomers of each other represent the same structural isomer. Enantiomers Enantiomers, also known as optical isomers, are two stereoisomers that are related to each other by a reflection: they are mirror images of each other that are non-superposable. Human hands are a macroscopic analog of this. Every stereogenic center in one has the opposite configuration in the other. Two compounds that are enantiomers of each other have the same physical properties, except for the direction in which they rotate polarized light and how they interact with different optical isom ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Variations On The Bucherer-Bergs Reaction
Variation or Variations may refer to: Science and mathematics * Variation (astronomy), any perturbation of the mean motion or orbit of a planet or satellite, particularly of the moon * Genetic variation, the difference in DNA among individuals or the differences between populations ** Human genetic variation, genetic differences in and among populations of humans * Magnetic variation, difference between magnetic north and true north, measured as an angle * ''p''-variation in mathematical analysis, a family of seminorms of functions * Coefficient of variation in probability theory and statistics, a standardized measure of dispersion of a probability distribution or frequency distribution * Total variation in mathematical analysis, a way of quantifying the change in a function over a subset of \mathbb^n or a measure space * Calculus of variations in mathematical analysis, a method of finding maxima and minima of functionals Arts * Variation (ballet) or pas seul, solo dance ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Methanol
Methanol (also called methyl alcohol and wood spirit, amongst other names) is an organic chemical and the simplest aliphatic alcohol, with the formula C H3 O H (a methyl group linked to a hydroxyl group, often abbreviated as MeOH). It is a light, volatile, colourless, flammable liquid with a distinctive alcoholic odour similar to that of ethanol (potable alcohol). A polar solvent, methanol acquired the name wood alcohol because it was once produced chiefly by the destructive distillation of wood. Today, methanol is mainly produced industrially by hydrogenation of carbon monoxide. Methanol consists of a methyl group linked to a polar hydroxyl group. With more than 20 million tons produced annually, it is used as a precursor to other commodity chemicals, including formaldehyde, acetic acid, methyl tert-butyl ether, methyl benzoate, anisole, peroxyacids, as well as a host of more specialised chemicals. Occurrence Small amounts of methanol are present in normal, healthy hu ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Ammonium Cyanide
Ammonium cyanide is an unstable inorganic compound with the formula NH4CN. Uses Ammonium cyanide is generally used in organic synthesis. Being unstable, it is not shipped or sold commercially. Preparation Ammonium cyanide is prepared in solution by bubbling hydrogen cyanide into aqueous ammonia at a low temperature : HCN + NH3 (aq) → NH4CN (aq) It may be prepared by the reaction of calcium cyanide and ammonium carbonate: : Ca(CN)2 + (NH4)2CO3 → 2 NH4CN + CaCO3 In dry state, ammonium cyanide is made by heating a mixture of potassium cyanide or potassium ferrocyanide with ammonium chloride and condensing the vapours into ammonium cyanide crystals: : KCN + NH4Cl → NH4CN + KCl Reactions Ammonium cyanide decomposes to ammonia and hydrogen cyanide, often forming a black polymer of hydrogen cyanide: : NH4CN → NH3 + HCN It undergoes salt metathesis reaction in solution with a number of metal salts to form metal–cyanide complexes. Reaction with ketones and aldehydes yield ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Carbon Disulfide
Carbon disulfide (also spelled as carbon disulphide) is a neurotoxic, colorless, volatile liquid with the formula and structure . The compound is used frequently as a building block in organic chemistry as well as an industrial and chemical non-polar solvent. It has an "ether-like" odor, but commercial samples are typically contaminated with foul-smelling impurities.. It is of comparable toxicity to carbon monoxide. History In 1796, the German chemist Wilhelm August Lampadius (1772–1842) first prepared carbon disulfide by heating pyrite with moist charcoal. He called it "liquid sulfur" (''flüssig Schwefel''). The composition of carbon disulfide was finally determined in 1813 by the team of the Swedish chemist Jöns Jacob Berzelius (1779–1848) and the Swiss-British chemist Alexander Marcet (1770–1822). Their analysis was consistent with an empirical formula of CS2. Occurrence, manufacture, properties Small amounts of carbon disulfide are released by volcanic eruptio ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Ultrasonics Sonochemistry
Ultrasound is sound waves with frequencies higher than the upper audible limit of human hearing. Ultrasound is not different from "normal" (audible) sound in its physical properties, except that humans cannot hear it. This limit varies from person to person and is approximately 20 kilohertz (20,000 hertz) in healthy young adults. Ultrasound devices operate with frequencies from 20 kHz up to several gigahertz. Ultrasound is used in many different fields. Ultrasonic devices are used to detect objects and measure distances. Ultrasound imaging or sonography is often used in medicine. In the nondestructive testing of products and structures, ultrasound is used to detect invisible flaws. Industrially, ultrasound is used for cleaning, mixing, and accelerating chemical processes. Animals such as bats and porpoises use ultrasound for locating prey and obstacles. History Acoustics, the science of sound, starts as far back as Pythagoras in the 6th century BC, who wrote on ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  




Chemical Diversity
Chemical Diversity (ChemDiv) is a US contract research organization headquartered in San Diego, California. It provides services to pharmaceutical and biotech companies for their research and development programs. ChemDiv has helped clients develop treatments and drugs for central nervous system, oncology, inflammation, metabolic, infectious and other diseases. Services include identification of a biological target ( protein production, assay development) to clinical drug candidates (ADME ADME is an abbreviation in pharmacokinetics and pharmacology for " absorption, distribution, metabolism, and excretion", and describes the disposition of a pharmaceutical compound within an organism. The four criteria all influence the drug le .../DMPK, toxicity and safety studies, efficacy models) to proof of concept and pivotal clinical trials of drug candidates (Phase I, II, III, IV) and market access assistance. ChemDiv started in 1990 as a chemistry provider and has since become a f ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Tetrahedron Lett
''Tetrahedron Letters'' is a weekly international journal for rapid publication of full original research papers in the field of organic chemistry. According to the ''Journal Citation Reports'', the journal has a 2020 impact factor of 2.415. Indexing ''Tetrahedron Letters'' is indexed in: References See also *''Tetrahedron In geometry, a tetrahedron (plural: tetrahedra or tetrahedrons), also known as a triangular pyramid, is a polyhedron composed of four triangular faces, six straight edges, and four vertex corners. The tetrahedron is the simplest of all the o ...'' *'' Tetrahedron: Asymmetry'' Chemistry journals Weekly journals Publications established in 1959 Elsevier academic journals {{chem-journal-stub ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


picture info

Electrophile
In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. Because electrophiles accept electrons, they are Lewis acids. Most electrophiles are positively charged, have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons. Electrophiles mainly interact with nucleophiles through addition and substitution reactions. Frequently seen electrophiles in organic syntheses include cations such as H+ and NO+, polarized neutral molecules such as HCl, alkyl halides, acyl halides, and carbonyl compounds, polarizable neutral molecules such as Cl2 and Br2, oxidizing agents such as organic peracids, chemical species that do not satisfy the octet rule such as carbenes and radicals, and some Lewis acids such as BH3 and DIBAL. Organic chemistry Addition of halogens These occur between alkenes and electrophiles, often halogens as in halogen addition reactions. Common reactions i ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]  


Aziridine
Aziridine is an organic compound consisting of the three-membered heterocycle . It is a colorless, toxic, volatile liquid that is of significant practical interest. Aziridine was discovered in 1888 by the chemist Siegmund Gabriel. Its derivatives, also referred to as aziridines, are of broader interest in medicinal chemistry. Structure The bond angles in aziridine are approximately 60°, considerably less than the normal hydrocarbon bond angle of 109.5°, which results in angle strain as in the comparable cyclopropane and ethylene oxide molecules. A banana bond model explains bonding in such compounds. Aziridine is less basic than acyclic aliphatic amines, with a pKa of 7.9 for the conjugate acid, due to increased s character of the nitrogen free electron pair. Angle strain in aziridine also increases the barrier to nitrogen inversion. This barrier height permits the isolation of separate ''invertomers'', for example the ''cis'' and ''trans'' invertomers of ''N''-chloro- ...
[...More Info...]      
[...Related Items...]     OR:     [Wikipedia]   [Google]   [Baidu]