1,2-rearrangement
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1,2-rearrangement
A 1,2-rearrangement or 1,2-migration or 1,2-shift or Whitmore 1,2-shift is an organic reaction where a substituent moves from one atom to another atom in a chemical compound. In a 1,2 shift the movement involves two adjacent atoms but moves over larger distances are possible. In the example below the substituent R moves from carbon atom C2 to C3. The rearrangement is intramolecular and the starting compound and reaction product are structural isomers. The 1,2-rearrangement belongs to a broad class of chemical reactions called rearrangement reactions. A rearrangement involving a hydrogen atom is called a 1,2-hydride shift. If the substituent being rearranged is an alkyl group, it is named according to the alkyl group's anion: i.e. 1,2-methanide shift, 1,2-ethanide shift, etc. Reaction mechanism A 1,2-rearrangement is often initialised by the formation of a reactive intermediate such as: *a carbocation by heterolysis in a nucleophilic rearrangement or anionotropic rearra ...
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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 ...
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Heinrich Otto Wieland
Heinrich Otto Wieland (; 4 June 1877 – 5 August 1957) was a German chemist. He won the 1927 Nobel Prize in Chemistry for his research into the bile acids. Career In 1901 Wieland received his doctorate at the University of Munich while studying under Johannes Thiele. In 1904 he completed his habilitation, then continued to teach at the university and starting in 1907 was a consultant for Boehringer Ingelheim. In 1914 he became associate professor for special topics in organic chemistry, and director of the Organic Division of the State Laboratory in Munich. From 1917 to 1918 Wieland worked in the service of the (KWI) Kaiser Wilhelm Institute for Physical Chemistry and Electrochemistry in Dahlem then led by Fritz Haber as an alternative to regular military service. There he was involved in weapons research for instance finding new synthetic routes for mustard gas. He is also credited with the first synthesis of Adamsite. From 1913 to 1921, he was Professor at the Technic ...
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Benzilic Acid Rearrangement
The benzilic acid rearrangement is formally the 1,2-rearrangement of 1,2-diketones to form α- hydroxy–carboxylic acids using a base. This reaction receives its name from the reaction of benzil with potassium hydroxide to form benzilic acid. First performed by Justus von Liebig in 1838, it is the first reported example of a rearrangement reaction.Nerve Agent Precursors: Benzilic acid and Methyl Benzilate
, Factsheets on Chemical and Biological Warfare Agents, Chemical precursors.
It has become a classic reaction in organic synthesis and has been reviewed many times before. It can be viewed as an intramolecular

Organic Reaction
Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, Mechanistic Organic Photochemistry, photochemical reactions and organic redox reaction, redox reactions. In organic synthesis, organic reactions are used in the construction of new organic molecules. The production of many man-made chemicals such as drugs, plastics, food additives, fabrics depend on organic reactions. The oldest organic reactions are combustion of organic fuels and saponification of fats to make soap. Modern organic chemistry starts with the Wöhler synthesis in 1828. In the history of the Nobel Prize in Chemistry awards have been given for the invention of specific organic reactions such as the Grignard reaction in 1912, the Diels-Alder reaction in 1950, the Wittig reaction in 1979 and olefin metathesis in 2005. Classifications Organic c ...
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Wagner–Meerwein Rearrangement
A Wagner–Meerwein rearrangement is a class of carbocation 1,2-rearrangement reactions in which a hydrogen, alkyl or aryl group migrates from one carbon to a neighboring carbon. They can be described as cationic ,2sigmatropic rearrangements, proceeding suprafacially and with stereochemical retention. As such, a Wagner–Meerwein shift is a thermally allowed pericyclic process with the Woodward-Hoffmann symbol ω0s_+_σ2s.html" ;"title="sub>ω0s + σ2s">sub>ω0s + σ2s They are usually facile, and in many cases, they can take place at temperatures as low as –120 °C. The reaction is named after the Russian chemist Yegor Yegorovich Vagner; he had German origin and published in German journals as Georg Wagner; and Hans Meerwein. Several reviews have been published. The rearrangement was first discovered in bicyclic terpenes for example the conversion of isoborneol to camphene: The story of the rearrangement reveals that many scientists were puzzled with this and relate ...
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Frank C
Frank or Franks may refer to: People * Frank (given name) * Frank (surname) * Franks (surname) * Franks, a medieval Germanic people * Frank, a term in the Muslim world for all western Europeans, particularly during the Crusades - see Farang Currency * Liechtenstein franc or frank, the currency of Liechtenstein since 1920 * Swiss franc or frank, the currency of Switzerland since 1850 * Westphalian frank, currency of the Kingdom of Westphalia between 1808 and 1813 * The currencies of the German-speaking cantons of Switzerland (1803–1814): ** Appenzell frank ** Argovia frank ** Basel frank ** Berne frank ** Fribourg frank ** Glarus frank ** Graubünden frank ** Luzern frank ** Schaffhausen frank ** Schwyz frank ** Solothurn frank ** St. Gallen frank ** Thurgau frank ** Unterwalden frank ** Uri frank ** Zürich frank Places * Frank, Alberta, Canada, an urban community, formerly a village * Franks, Illinois, United States, an unincorporated community * Franks, Missouri, United ...
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Nitrene
In chemistry, a nitrene or imene () is the nitrogen analogue of a carbene. The nitrogen atom is uncharged and univalent, so it has only 6 electrons in its valence level—two covalent bonded and four non-bonded electrons. It is therefore considered an electrophile due to the unsatisfied octet. A nitrene is a reactive intermediate and is involved in many chemical reactions. The simplest nitrene, HN, is called imidogen, and that term is sometimes used as a synonym for the nitrene class. Electron configuration In the simplest case, the linear N–H molecule (imidogen) has its nitrogen atom sp hybridized, with two of its four non-bonded electrons as a lone pair in an sp orbital and the other two occupying a degenerate pair of p orbitals. The electron configuration is consistent with Hund's rule: the low energy form is a triplet with one electron in each of the p orbitals and the high energy form is the singlet with an electron pair filling one p orbital and the other p orbit ...
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Mole (unit)
The mole, symbol mol, is the unit of amount of substance in the International System of Units (SI). The quantity amount of substance is a measure of how many elementary entities of a given substance are in an object or sample. The mole is defined as containing exactly elementary entities. Depending on what the substance is, an elementary entity may be an atom, a molecule, an ion, an ion pair, or a subatomic particle such as an electron. For example, 10 moles of water (a chemical compound) and 10 moles of mercury (a chemical element), contain equal amounts of substance and the mercury contains exactly one atom for each molecule of the water, despite the two having different volumes and different masses. The number of elementary entities in one mole is known as the Avogadro number, which is the approximate number of nucleons (protons or neutrons) in one gram of ordinary matter. The previous definition of a mole was simply the number of elementary entities equal to that of 12 gram ...
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Calorie
The calorie is a unit of energy. For historical reasons, two main definitions of "calorie" are in wide use. The large calorie, food calorie, or kilogram calorie was originally defined as the amount of heat needed to raise the temperature of one kilogram of water by one degree Celsius (or one kelvin). The small calorie or gram calorie was defined as the amount of heat needed to cause the same increase in one gram of water. Thus, 1 large calorie is equal to 1000 small calories. In nutrition and food science, the term ''calorie'' and the symbol ''cal'' almost always refers to the large unit. It is generally used in publications and package labels to express the energy value of foods in per serving or per weight, recommended dietary caloric intake, metabolic rates, etc. Some authors recommend the spelling ''Calorie'' and the symbol ''Cal'' (both with a capital C) to avoid confusion; however, this convention is often ignored. In physics and chemistry the word ''calorie'' and i ...
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Aryl Radical
An aryl radical in organic chemistry is a reactive intermediate and an arene compound incorporating one free radical carbon atom as part of the ring structure. As such it is the radical counterpart of the arenium ion. The parent compound is the phenyl radical .''Minireview Intermolecular Olefin Functionalisation Involving Aryl Radicals Generated from Arenediazonium Salts'' Markus R. Heinrich Chemistry - A European Journal 2008 volume 15 issue 4, pages 820 - 833 Aryl radicals are intermediates in certain organic reactions. Synthesis Aryl radicals can be obtained via aryl diazonium salts. Alternatives for these salts are certain aryl triazenes and aryl hydrazines. Aryl bromides and iodides can be converted to aryl radicals via tributyltin hydride and related compounds and silyl hydrides. Aryl halides can also be converted via electrochemical cathodic reduction The mushroom ''Stephanospora caroticolor'' is suspected to generate an aryl radical as part of its biological chemical defe ...
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Electron Spin Resonance
Electron paramagnetic resonance (EPR) or electron spin resonance (ESR) spectroscopy is a method for studying materials that have unpaired electrons. The basic concepts of EPR are analogous to those of nuclear magnetic resonance (NMR), but the spins excited are those of the electrons instead of the atomic nuclei. EPR spectroscopy is particularly useful for studying metal complexes and organic radicals. EPR was first observed in Kazan State University by Soviet physicist Yevgeny Zavoisky in 1944, and was developed independently at the same time by Brebis Bleaney at the University of Oxford. Theory Origin of an EPR signal Every electron has a magnetic moment and spin quantum number s = \tfrac , with magnetic components m_\mathrm = + \tfrac or m_\mathrm = - \tfrac . In the presence of an external magnetic field with strength B_\mathrm , the electron's magnetic moment aligns itself either antiparallel ( m_\mathrm = - \tfrac ) or parallel ( m_\mathrm = + \tfrac ) to the fi ...
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