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Boyland–Sims Oxidation
The Boyland–Sims oxidation is the chemical reaction of anilines with alkaline potassium persulfate, which after hydrolysis forms ''ortho''-hydroxyl anilines. The reaction is generally performed in water at room temperatures or below, using equimolar quantities of reagents. The ''ortho''-isomer is formed predominantly. However, the ''para''-sulfate is formed in small amounts with certain anilines. Scope and mechanism The reaction is disadvantaged by moderate to low chemical yields, but is simple to perform and uses mild conditions. Some competitive oxidation of the nitrogen has been observed. Behrman has shown that the first intermediate in the Boyland–Sims oxidation is the formation of an arylhydroxylamine-O-sulfate (2). Rearrangement of this zwitterionic intermediate forms the ortho- sulfate (5), which then hydrolyses to form the ortho-hydroxyl aniline. See also * Elbs persulfate oxidation The Elbs persulfate oxidation is the organic reaction of phenols with alkaline po ...
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Chemical Reaction
A chemical reaction is a process that leads to the IUPAC nomenclature for organic transformations, chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and breaking of chemical bonds between atoms, with no change to the Atomic nucleus, nuclei (no change to the elements present), and can often be described by a chemical equation. Nuclear chemistry is a sub-discipline of chemistry that involves the chemical reactions of unstable and radioactive Chemical element, elements where both electronic and nuclear changes can occur. The substance (or substances) initially involved in a chemical reaction are called reagent, reactants or reagents. Chemical reactions are usually characterized by a chemical change, and they yield one or more Product (chemistry), products, which usually have properties different from the reactants. Reactions often consist of a sequence o ...
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Aniline
Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aromatic ring attached to an amine. It is a broad class of compounds that encompasses aniline Aniline is an organic compound with the formula C6 H5 NH2. Consi .... It is an industrially significant Commodity chemicals, commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It Combustion, ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans. Relative to benzene, it is electron-rich. It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone ...
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Potassium Persulfate
Potassium persulfate is the inorganic compound with the formula K2 S2O8. Also known as potassium peroxydisulfate, it is a white solid that is sparingly soluble in cold water, but dissolves better in warm water. This salt is a powerful oxidant, commonly used to initiate polymerizations. Structure The sodium and potassium salts are very similar. In the potasium salt, the O-O distance is 1.495Å. The individual sulfate groups are tetrahedral, with three short S-O distances near 1.43 and one long S-O bond at 1.65Å. Preparation Potassium persulfate can be prepared by electrolysis of a cold solution potassium bisulfate in sulfuric acid at a high current density.{{cite book, last=Brauer, first=Georg, title=Handbook of Preparative Inorganic Chemistry , volume=1 , edition=2nd , year=1963 , publisher=Academic Press , location=New York , isbn=978-0121266011 , page=392 , url=https://books.google.com/books?id=TLYatwAACAAJ&q=Handbook+of+Preparative+Inorganic+Chemistry : 2 KHSO4 → K2S2O ...
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Hydrolysis
Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolysis is the cleavage of biomolecules where a water molecule is consumed to effect the separation of a larger molecule into component parts. When a carbohydrate is broken into its component sugar molecules by hydrolysis (e.g., sucrose being broken down into glucose and fructose), this is recognized as saccharification. Hydrolysis reactions can be the reverse of a condensation reaction in which two molecules join into a larger one and eject a water molecule. Thus hydrolysis adds water to break down, whereas condensation builds up by removing water. Types Usually hydrolysis is a chemical process in which a molecule of water is added to a substance. Sometimes this addition causes both the substance and w ...
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Chemical Yield
In chemistry, yield, also referred to as reaction yield, is a measure of the quantity of moles of a product formed in relation to the reactant consumed, obtained in a chemical reaction, usually expressed as a percentage. Yield is one of the primary factors that scientists must consider in organic and inorganic chemical synthesis processes. In chemical reaction engineering, "yield", "conversion" and "selectivity" are terms used to describe ratios of how much of a reactant was consumed (conversion), how much desired product was formed (yield) in relation to the undesired product (selectivity), represented as X, Y, and S. Definitions In chemical reaction engineering, "yield", "conversion" and "selectivity" are terms used to describe ratios of how much of a reactant has reacted—conversion, how much of a desired product was formed—yield, and how much desired product was formed in ratio to the undesired product—selectivity, represented as X,S, and Y. According to the ''Ele ...
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Zwitterion
In chemistry, a zwitterion ( ; ), also called an inner salt or dipolar ion, is a molecule that contains an equal number of positively- and negatively-charged functional groups. : With amino acids, for example, in solution a chemical equilibrium will be established between the "parent" molecule and the zwitterion. Betaines are zwitterions that cannot isomerize to an all-neutral form, such as when the positive charge is located on a quaternary ammonium group. Similarly, a molecule containing a phosphonium group and a carboxylate group cannot isomerize. Amino acids The equilibrium is established in two stages. In the first stage, a proton is transferred from the carboxyl group to a water molecule: :H2N(R)CO2H + H2O H2N(R)CO2- + H3O+ In the second stage, a proton is transferred from the hydronium ion to the amine group: :H2N(R)CO2- + H3O+ H3N+ (R)CO2- + H2O Overall, the reaction is an isomerization reaction :H2N(R)CO2H H3N+ (R)CO2- The ratio of the concentrations of the two spec ...
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Aromatic Ortho Substituent
In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to saturated compounds having single bonds, and other geometric or connective non-cyclic arrangements with the same set of atoms. Aromatic rings are very stable and do not break apart easily. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have enhanced stability. The term ''aromaticity'' with this meaning is historically related to the concept of having an aroma, but is a distinct property from that meaning. Since the most common aromatic compounds are derivatives of benzene (an aromatic hydrocarbon common in petroleum and its distillates), the word ''aromatic'' occasionally refers informally to benzene derivatives, and so it was first defined. Nevertheless, many non-ben ...
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Elbs Persulfate Oxidation
The Elbs persulfate oxidation is the organic reaction of phenols with alkaline potassium persulfate to form ''para''-diphenols. The reaction is generally performed in water at room temperatures or below, using equimolar quantities of reagents. Several reviews have been published. Scope and mechanism The reaction is disadvantaged by moderate to low chemical yields with recovery of starting material and complete consumption of the persulfate. It is suggested that the phenol in many cases is a catalyst converting the persulfate into a sulfate. Despite this, the Elbs reaction remains generally useful in a research setting, as it is simple to perform and is tolerant of a wide range of other functional groups, which are not oxidised under these conditions. A reaction mechanism has been postulated which accounts for the observed ''para'' substitution featuring the tautomeric ''para'' carbanion of the starting phenolate ion:{{cite journal , author = Behrman, E. J. , title = The Elbs a ...
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Organic Oxidation Reactions
Organic may refer to: * Organic, of or relating to an organism, a living entity * Organic, of or relating to an anatomical organ Chemistry * Organic matter, matter that has come from a once-living organism, is capable of decay or is the product of decay, or is composed of organic compounds * Organic compound, a compound that contains carbon ** Organic chemistry, chemistry involving organic compounds Farming, certification and products * Organic farming, agriculture conducted according to certain standards, especially the use of stated methods of fertilization and pest control * Organic certification, accreditation process for producers of organically-farmed products * Organic horticulture, the science and art of growing fruits, vegetables, flowers, or ornamental plants by following the essential principles of organic agriculture * Organic products, "organics": ** Organic food, food produced from organic farming methods and often certified organic according to organic farming stan ...
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