Willgerodt Rearrangement
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Willgerodt Rearrangement
The Willgerodt rearrangement or Willgerodt reaction is an organic reaction converting an aryl alkyl ketone, alkyne, or alkene to the corresponding amide by reaction with ammonium polysulfide, named after Conrad Willgerodt. The formation of the corresponding carboxylic acid is a side reaction. When the alkyl group is an aliphatic chain (n typically 0 to 5), multiple reactions take place with the amide group always ending up at the terminal end. An example with modified reagents (sulfur, concentrated ammonium hydroxide and pyridine) is the conversion of acetophenone to 2-phenylacetamide and phenylacetic acid Willgerodt–Kindler reaction The related Willgerodt–Kindler reaction takes place with elemental sulfur and an amine like morpholine. The initial product is a thioacetamide for example that of acetophenone which can again be hydrolyzed to the amide. The reaction is named after Karl Kindler. Reaction mechanism A possible reaction mechanism for the Kindler variation'' ...
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Conrad Willgerodt
Conrad Heinrich Christoph Willgerodt (November 2, 1841 – December 19, 1930) was a German chemist who first described the Willgerodt reaction. Alongside the Willgerodt reaction, he had also discovered Iodosobenzene and chlorobutanol. As for his career, Conrad Willgerodt was a professor at the University of Freiburg The University of Freiburg (colloquially german: Uni Freiburg), officially the Albert Ludwig University of Freiburg (german: Albert-Ludwigs-Universität Freiburg), is a public university, public research university located in Freiburg im Breisg .... References External links * 1841 births 1930 deaths 19th-century German chemists University of Freiburg faculty People from Goslar (district) People from the Duchy of Brunswick 20th-century German chemists {{Germany-chemist-stub ...
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Karl Kindler
Karl may refer to: People * Karl (given name), including a list of people and characters with the name * Karl der Große, commonly known in English as Charlemagne * Karl Marx, German philosopher and political writer * Karl of Austria, last Austrian Emperor * Karl (footballer) (born 1993), Karl Cachoeira Della Vedova Júnior, Brazilian footballer In myth * Karl (mythology), in Norse mythology, a son of Rig and considered the progenitor of peasants (churl) * ''Karl'', giant in Icelandic myth, associated with Drangey island Vehicles * Opel Karl, a car * ST ''Karl'', Swedish tugboat requisitioned during the Second World War as ST ''Empire Henchman'' Other uses * Karl, Germany, municipality in Rhineland-Palatinate, Germany * '' Karl-Gerät'', AKA Mörser Karl, 600mm German mortar used in the Second World War * KARL project, an open source knowledge management system * Korean Amateur Radio League, a national non-profit organization for amateur radio enthusiasts in South Korea * KARL ...
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Stork Enamine Alkylation
The Stork enamine alkylation involves the addition of an enamine to a Michael acceptor (e.g, an α,β -unsaturated carbonyl compound) or another electrophilic alkylation reagent to give an alkylated iminium product, which is hydrolyzed by dilute aqueous acid to give the alkylated ketone or aldehyde. Since enamines are generally produced from ketones or aldehydes, this overall process (known as the Stork enamine synthesis) constitutes a selective monoalkylation of a ketone or aldehyde, a process that may be difficult to achieve directly. The Stork enamine synthesis: # formation of an enamine from a ketone # addition of the enamine to an alpha, beta-unsaturated aldehyde or ketone # hydrolysis of the enamine back to a ketone The reaction also applies to acyl halides as electrophiles, which results in the formation of 1,3-diketones (Stork acylation). It is also effective for activated sp3 alkyl electrophiles, including benzylic, allylic/propargylic, α-carbonyl (e.g., bromoace ...
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Conjugate Addition
Nucleophilic conjugate addition is a type of organic reaction. Ordinary nucleophilic additions or 1,2-nucleophilic additions deal mostly with additions to carbonyl compounds. Simple alkene compounds do not show 1,2 reactivity due to lack of polarity, unless the alkene is activated with special substituents. With α,β-unsaturated carbonyl compounds such as cyclohexenone it can be deduced from resonance structures that the β position is an electrophilic site which can react with a nucleophile. The negative charge in these structures is stored as an alkoxide anion. Such a nucleophilic addition is called a nucleophilic conjugate addition or 1,4-nucleophilic addition. The most important active alkenes are the aforementioned conjugated carbonyls and acrylonitriles. Reaction mechanism Conjugate addition is the vinylogous counterpart of direct nucleophilic addition. A nucleophile reacts with a α,β-unsaturated carbonyl compound in the β position. The negative charge carried by the n ...
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Enamine
An enamine is an unsaturated compound derived by the condensation of an aldehyde or ketone with a secondary amine. Enamines are versatile intermediates. : The word "enamine" is derived from the affix ''en''-, used as the suffix of alkene, and the root ''amine''. This can be compared with enol, which is a functional group containing both alkene (''en''-) and alcohol (-''ol''). Enamines are considered to be nitrogen analogs of enols. If one of the nitrogen substituents is a hydrogen atom, H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautomerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom. Enamines are both good nucleophiles and good bases. Their behavior as carbon-based nucleophiles is explained with reference to the following reson ...
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Alkylimino-de-oxo-bisubstitution
In organic chemistry, alkylimino-de-oxo-bisubstitution is the organic reaction of carbonyl compounds with amines to imines. The reaction name is based on the IUPAC Nomenclature for Transformations. The reaction is acid catalyzed and the reaction type is nucleophilic addition of the amine to the carbonyl compound followed by transfer of a proton from nitrogen to oxygen to a stable hemiaminal or carbinolamine. With primary amines water is lost in an elimination reaction to an imine. With aryl amines especially stable Schiff bases are formed. Reaction mechanism The reaction steps are reversible reactions and the reaction is driven to completion by removal of water e.g. by azeotropic distillation, molecular sieves or titanium tetrachloride. Primary amines react through an unstable hemiaminal intermediate which then splits off water. : Secondary amines do not lose water easily because they do not have a proton available and instead they often react further to an aminal: : or whe ...
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Kindler Mechanism
Kindler is a surname. Notable people with the surname include: *Andy Kindler (born 1956), American stand-up comedian * Damian Kindler (born 1968), Australian-born Canadian writer and producer *Hans Kindler (1892–1949), American cellist and conductor *Jeff Kindler, the CEO of the Pfizer corporation *Sven-Christian Kindler (born 1985), German politician See also *Kindler syndrome Kindler syndrome (also known as "bullous acrokeratotic poikiloderma of Kindler and Weary",) is a rare congenital disease of the skin caused by a mutation in the KIND1 gene. Symptoms and signs Infants and young children with Kindler syndrome hav ..., rare congenital disease of the skin caused by a mutation in the KIND1 gene * Kindler v. Canada (Minister of Justice), landmark decision of the Supreme Court of Canada {{surname, Kindler German-language surnames ...
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Reaction Mechanism
In chemistry, a reaction mechanism is the step by step sequence of elementary reactions by which overall chemical change occurs. A chemical mechanism is a theoretical conjecture that tries to describe in detail what takes place at each stage of an overall chemical reaction. The detailed steps of a reaction are not observable in most cases. The conjectured mechanism is chosen because it is thermodynamically feasible, and has experimental support in isolated intermediates (see next section) or other quantitative and qualitative characteristics of the reaction. It also describes each reactive intermediate, activated complex, and transition state, and which bonds are broken (and in what order), and which bonds are formed (and in what order). A complete mechanism must also explain the reason for the reactants and catalyst used, the stereochemistry observed in reactants and products, all products formed and the amount of each. The electron or arrow pushing method is often used in i ...
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Kindler Mod Willgerodt
Kindler is a surname. Notable people with the surname include: *Andy Kindler (born 1956), American stand-up comedian * Damian Kindler (born 1968), Australian-born Canadian writer and producer *Hans Kindler (1892–1949), American cellist and conductor *Jeff Kindler, the CEO of the Pfizer corporation *Sven-Christian Kindler (born 1985), German politician See also *Kindler syndrome Kindler syndrome (also known as "bullous acrokeratotic poikiloderma of Kindler and Weary",) is a rare congenital disease of the skin caused by a mutation in the KIND1 gene. Symptoms and signs Infants and young children with Kindler syndrome hav ..., rare congenital disease of the skin caused by a mutation in the KIND1 gene * Kindler v. Canada (Minister of Justice), landmark decision of the Supreme Court of Canada {{surname, Kindler German-language surnames ...
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Organic Syntheses
''Organic Syntheses'' is a peer-reviewed scientific journal that was established in 1921. It publishes detailed and checked procedures for the synthesis of organic compounds. A unique feature of the review process is that all of the data and experiments reported in an article must be successfully repeated in the laboratory of a member of the editorial board as a check for reproducibility prior to publication. The journal is published by Organic Syntheses, Inc., a non-profit corporation. An annual print version is published by John Wiley & Sons on behalf of Organic Syntheses, Inc. History Prior to World War I, work on synthetic organic chemistry in the United States had been quite limited, and most of the reagents used in laboratories had to be imported from Europe. When export stoppages and trade embargoes cut off this source, Clarence Derick, a professor of chemistry at University of Illinois at Urbana-Champaign, began an effort to synthesize these needed chemicals in industr ...
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Thioacetamide
Thioacetamide is an organosulfur compound with the chemical formula, formula carbon, C2hydrogen, H5nitrogen, Nsulfur, S. This white crystalline solid is soluble in water and serves as a source of sulfide ions in the synthesis of organic and inorganic compounds. It is a prototypical thioamide. Research Thioacetamide is known to induce acute or chronic liver disease (fibrosis and cirrhosis) in the experimental animal model. Its administration in rat induces hepatic encephalopathy, metabolic acidosis, increased levels of transaminases, abnormal coagulopathy, and centrilobular necrosis, which are the main features of the clinical chronic liver disease so thioacetamide can precisely replicate the initiation and progression of human liver disease in an experimental animal model. Coordination chemistry Thioacetamide is widely used in classical qualitative inorganic analysis as an in situ source for sulfide ions. Thus, treatment of aqueous solutions of many metal cations to a solution ...
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Morpholine
Morpholine is an organic chemical compound having the chemical formula O( C H2CH2)2 NH. This heterocycle features both amine and ether functional groups. Because of the amine, morpholine is a base; its conjugate acid is called morpholinium. For example, treating morpholine with hydrochloric acid makes the salt morpholinium chloride. It is a colorless liquid with a weak, ammonia- or fish-like odor. The naming of morpholine is attributed to Ludwig Knorr, who incorrectly believed it to be part of the structure of morphine. Production Morpholine is often produced industrially by the dehydration of diethanolamine with sulfuric acid: : Uses Industrial applications Morpholine is a common additive, in parts per million concentrations, for pH adjustment in both fossil fuel and nuclear power plant steam systems. Morpholine is used because its volatility is about the same as water, so once it is added to the water, its concentration becomes distributed rather evenly in both the water a ...
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