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Hofmann–Martius Rearrangement
The Hofmann–Martius rearrangement in organic chemistry is a rearrangement reaction converting an N-alkylated aniline to the corresponding aromatic ortho substituent, ortho and / or aromatic para substituent, para arene compound, aryl-alkylated aniline. The reaction requires heat, and the catalyst is an acid like hydrochloric acid. : When the catalyst is a metal halide the reaction is also called the Reilly–Hickinbottom rearrangement. The reaction is also known to work for aryl ethers and two conceptually related reactions are the Fries rearrangement and the Fischer–Hepp rearrangement. Its reaction mechanism centers around dissociation of the reactant with the positively charged organic residue R attacking the aniline ring in a Friedel–Crafts alkylation. In one study this rearrangement was applied to a 3-N(CH3)(C6H5)-2-oxindole:heating 1 in toluene at 80 °C gives 30% 2-o (ortho) and 37% 2-p (para) : The reaction is named after German chemists August Wilhelm von Hofmann ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Organic Chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, J.; Greeves, N. and Warren, S. (2012) ''Organic Chemistry''. Oxford University Press. pp. 1–15. . Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and via theoretical ( in silico) study. The range of chemicals studied in organic chemistry includes hydrocarbons (compounds containing only carbon and hydrogen) as well as compounds based on carbon, but also containing other elements, especially oxygen, nitrogen, sulfur, phosphorus (included in ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fischer–Hepp Rearrangement
The Fischer–Hepp rearrangement is a rearrangement reaction in which an aromatic N-nitroso or nitrosamine converts to a carbon nitroso compound: This organic reaction was first described by the German chemist Otto Philipp Fischer (1852–1932) and Eduard Hepp (June 11, 1851 – June 18, 1917) W Pötsch. ''Lexikon bedeutender Chemiker'' (VEB Bibliographisches Institut Leipzig, 1989) in 1886, and is of importance because para- NO secondary anilines cannot be prepared in a direct reaction. The rearrangement reaction takes place by reacting the nitrosamine precursor with hydrochloric acid. The chemical yield is generally good under these conditions, but often much poorer if a different acid is used. The exact reaction mechanism is unknown but there is evidence suggesting an intramolecular reaction. Sources''Named Things in Chemical Industry'' See also * Friedel–Crafts alkylation-like reactions: ** Hofmann-Martius rearrangement **Fries rearrangement The Fries rearrangement, n ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Carl Alexander Von Martius
Carl Alexander von Martius (born January 19, 1838, in Munich; died February 26, 1920, in Nonn by Bad Reichenhall) was a German chemist and entrepreneur. Life His father was botanist and explorer Carl Friedrich Philipp von Martius (1794–1868) and his mother was author Franziska von Stengel (1801–1843). In 1872, Martius married ''Margarete Veit'' (1853–1926). On February 16, 1903, Martius became by German king Wilhelm II a nobleman. Martius studied chemistry. At university he was member of student organisation '' Corps Bremensia''. He was a student of Justus von Liebig and university assistent August Wilhelm von Hofmann in Berlin. In 1863, Martius invented in Berlin azo dye Bismarck brown Y, which he named after german chancellor Otto von Bismarck. It is used in histology for staining tissues. In 1867, Martius invented in Berlin '' Dinitronaphthol'', which was later named after him as ''Martiusgelb''. In Berlin, together with German chemist Paul Mendelssohn Bartholdy h ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
August Wilhelm Von Hofmann
August Wilhelm von Hofmann (8 April 18185 May 1892) was a German chemist who made considerable contributions to organic chemistry. His research on aniline helped lay the basis of the aniline-dye industry, and his research on coal tar laid the groundwork for his student Charles Mansfield's practical methods for extracting benzene and toluene and converting them into nitro compounds and amines. Hofmann's discoveries include formaldehyde, hydrazobenzene, the isonitriles, and allyl alcohol. He prepared three ethylamines and tetraethylammonium compounds and established their structural relationship to ammonia. After studying under Justus von Liebig at the University of Giessen, Hofmann became the first director of the Royal College of Chemistry, now part of Imperial College London, in 1845. In 1865 he returned to Germany to accept a position at the University of Berlin as a teacher and researcher. After his return he co-founded the German Chemical Society (''Deutsche Chemische Gese ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Toluene
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent. As the solvent in some types of paint thinner, permanent markers, contact cement and certain types of glue, toluene is sometimes used as a recreational inhalant and has the potential of causing severe neurological harm. History The compound was first isolated in 1837 through a distillation of pine oil by the Polish chemist Filip Walter, who named it ''rétinnaphte''. In 1841, French chemist Henri Étienne Sainte-Claire Deville isolated a hydrocarbon from balsam of Tolu (an aromatic extract from the tropical Colombian tree ''Myroxylon balsamum''), which Deville recognized as similar to Wa ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
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 ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Fries Rearrangement
The Fries rearrangement, named for the German chemist Karl Theophil Fries, is a rearrangement reaction of a phenolic ester to a hydroxy aryl ketone by catalysis of Lewis acids. It involves migration of an acyl group of phenol ester to the aryl ring. The reaction is ortho and para selective and one of the two products can be favoured by changing reaction conditions, such as temperature and solvent. Mechanism Despite many efforts, a definitive reaction mechanism for the Fries rearrangement has not been determined. Evidence for inter- and intramolecular mechanisms have been obtained by crossover experiments with mixed reactants. The reaction progress is not dependent on solvent or substrate. A widely accepted mechanism involves a carbocation intermediate. In the first reaction step a Lewis acid for instance aluminium chloride co-ordinates to the carbonyl oxygen atom of the acyl group. This oxygen atom is more electron rich than the phenolic oxygen atom and is the preferred ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Rearrangement Reaction
In organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular. In the example below, the substituent R moves from carbon atom 1 to carbon atom 2: :\underset\ce\ce\underset\ce\ce Intermolecular rearrangements also take place. A rearrangement is not well represented by simple and discrete electron transfers (represented by curved arrows in organic chemistry texts). The actual mechanism of alkyl groups moving, as in Wagner-Meerwein rearrangement, probably involves transfer of the moving alkyl group fluidly along a bond, not ionic bond-breaking and forming. In pericyclic reactions, explanation by orbital interactions give a better picture than simple discrete electron transfers. It is, nevertheless, possible to draw the curv ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydrochloric Acid
Hydrochloric acid, also known as muriatic acid, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid Acid strength is the tendency of an acid, symbolised by the chemical formula HA, to dissociate into a proton, H+, and an anion, A-. The dissociation of a strong acid in solution is effectively complete, except in its most concentrated solutions .... It is a component of the gastric acid in the digestive systems of most animal species, including humans. Hydrochloric acid is an important laboratory reagent and industrial chemical. History In the early tenth century, the Persian physician and alchemist Abu Bakr al-Razi ( 865–925, Latin: Rhazes) conducted experiments with sal ammoniac (ammonium chloride) and vitriol (hydrated sulfates of various metals), which he distilled together, thus producing the gas hydrogen chloride. In doing so, al-Razi may have stumbled upon a primitive method ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
