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Ferrier Rearrangement
The Ferrier rearrangement is an organic reaction that involves a nucleophilic substitution reaction combined with an allylic shift in a glycal (a 2,3- unsaturated glycoside). It was discovered by the carbohydrate chemist Robert J. Ferrier. Mechanism In the first step, a delocalized allyloxocarbenium ion (2) is formed, typically with the aid of a Lewis acid like indium(III) chloride or boron trifluoride. This ion reacts in situ with an alcohol, yielding a mixture of the α (3) and β (4) anomers of the 2-glycoside, with the double bond shifted to position 3,4. Examples Modifications Forming of C-glycosides By replacing the alcohol with a silane, C-glycosides can be formed. With triethylsilane (R'=H), the reaction yields a 2,3-unsaturated deoxy sugar. Nitrogen analogue An analogous reaction with nitrogen as the heteroatom was described in 1984 for the synthesis of the antibiotic An antibiotic is a type of antimicrobial substance active against bacteria. I ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ferrier Carbocyclization
The Ferrier carbocyclization (or Ferrier II reaction) is an organic reaction that was first reported by the carbohydrate chemist Robert J. Ferrier in 1979. It is a metal-mediated rearrangement reaction, rearrangement of enol ether pyrans to cyclohexanones. Typically, this reaction is catalyzed by mercury (element), mercury salts, specifically mercury(II) chloride. Several reviews have been published. Reaction mechanism Ferrier proposed the following reaction mechanism: In this mechanism, the terminal olefin undergoes hydroxymercuration to produce the first intermediate, compound 2, a hemiacetal. Next, methanol is lost and the dicarbonyl compound cyclizes through an attack on the electrophilic aldehyde to form the carbocycle as the product. A downside to this reaction is that the loss of CH3OH at the anomeric position (carbon-1) results in a mixture of α- and β-anomers. The reaction also works for substituted alkenes (e. g. having an -Oacetyl, Ac group on the terminal alk ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Arkivoc
''Arkivoc'' (''Archive for Organic Chemistry'') is a peer-reviewed open access scientific journal covering all aspects of organic chemistry. It is published by the non-profit organization Arkat USA, which was established in 2000 through a personal donation from Alan R. Katritzky and Linde Katritzky. ''Arkivoc'' is the primary publication of Arkat USA. According to the ''Journal Citation Reports'', the journal has a 2014 impact factor The impact factor (IF) or journal impact factor (JIF) of an academic journal is a type of journal ranking. Journals with higher impact factor values are considered more prestigious or important within their field. The Impact Factor of a journa ... of 1.165, ranking it 37th out of 57 journals in the category "Chemistry, Organic". Abstracting and Indexing According to the Journal Citation Reports, the journal has a 2018 impact factor of 1.253. The journal is indexed in Web of Science: Science Citation Index Expanded. References External lin ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Triethylsilane
Triethylsilane is the organosilicon compound with the formula (C2H5)3SiH. It is a trialkylsilane. The Si-H bond is reactive. It was first discovered by Albert Ladenburg in 1872 among the products of reduction of tetraethyl orthosilicate with sodium and diethylzinc. He also prepared it by a stepwise reduction via ethoxytriethylsilane and named it silicoheptyl hydride, reflecting the idea of a silicon compound analogous to a seven-carbon hydrocarbon. This colorless liquid is used in organic synthesis as a reducing agent In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ). Examples of substances that are common reducing agents include hydrogen, carbon ... and as a precursor to silyl ethers. As one of the simplest trialkylsilanes that is a liquid at room temperature, triethylsilane is often used in studies of hydrosilylation catalysis. Additional reading * * * * ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Silane
Silane (Silicane) is an inorganic compound with chemical formula . It is a colorless, pyrophoric gas with a sharp, repulsive, pungent smell, somewhat similar to that of acetic acid. Silane is of practical interest as a precursor to elemental silicon. Silanes with alkyl groups are effective water repellents for mineral surfaces such as concrete and masonry. Silanes with both organic and inorganic attachments are used as coupling agents. They are commonly used to apply coatings to surfaces or as an adhesion promoter. Production Commercial-scale routes Silane can be produced by several routes. Typically, it arises from the reaction of hydrogen chloride with magnesium silicide: : It is also prepared from metallurgical-grade silicon in a two-step process. First, silicon is treated with hydrogen chloride at about 300 °C to produce trichlorosilane, HSiCl3, along with hydrogen gas, according to the chemical equation : The trichlorosilane is then converted to a mixture ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Benzyl Alcohol
Benzyl alcohol (also known as α-cresol) is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is useful as a solvent for its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide. Natural occurrences Benzyl alcohol is produced naturally by many plants and is commonly found in fruits and teas. It is also found in a variety of essential oils including jasmine, hyacinth and ylang-ylang. It is also found in castoreum from the castor sacs of beavers. Benzyl esters also occur naturally. Preparation Benzyl alcohol is produced industrially from toluene via ben ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Toluene
Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon with the chemical formula , often abbreviated as , where Ph stands for the phenyl group. It is a colorless, water Water is an inorganic compound with the chemical formula . It is a transparent, tasteless, odorless, and Color of water, nearly colorless chemical substance. It is the main constituent of Earth's hydrosphere and the fluids of all known liv ...-insoluble liquid with the odor associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group by a single bond. As such, its systematic IUPAC nomenclature of organic chemistry, 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 causin ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Ethanol
Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the pseudoelement symbol for ethyl group, ethyl. Ethanol is a Volatility (chemistry), volatile, flammable, colorless liquid with a characteristic wine-like odor and pungent taste. As a psychoactive depressant, it is the active ingredient in alcoholic beverages, and the second most consumed drug globally behind caffeine. Ethanol is naturally produced by the fermentation process of sugars by yeasts or via petrochemical processes such as ethylene hydration. Historically it was used as a general anesthetic, and has modern medical applications as an antiseptic, disinfectant, solvent for some medications, and antidote for methanol poisoning and ethylene glycol poisoning. It is used as a chemical solvent and in the Chemical synthesis, synthesis of orga ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Zinc Chloride
Zinc chloride is an Inorganic chemistry, inorganic chemical compound with the chemical formula, formula ZnCl2·''n''H2O, with ''n'' ranging from 0 to 4.5, forming water of hydration, hydrates. Zinc chloride, anhydrous and its hydrates, are colorless or white crystalline solids, and are highly Solubility, soluble in water. Five hydrates of zinc chloride are known, as well as four Polymorphism (materials science), polymorphs of anhydrous zinc chloride. All forms of zinc chloride are deliquescent. They can usually be produced by the reaction of zinc or its compounds with some form of hydrogen chloride. Anhydrous zinc compound is a Lewis acid, readily forming complexes with a variety of Lewis bases. Zinc chloride finds wide application in textile processing, flux (metallurgy), metallurgical fluxes, chemical synthesis of organic compounds, such as benzaldehyde, and processes to produce other compounds of zinc. History Zinc chloride has long been known but currently practiced industr ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Room Temperature
Room temperature, colloquially, denotes the range of air temperatures most people find comfortable indoors while dressed in typical clothing. Comfortable temperatures can be extended beyond this range depending on humidity, air circulation, and other factors. In certain fields, like science and engineering, and within a particular context, room temperature can mean different agreed-upon ranges. In contrast, ambient temperature is the actual temperature, as measured by a thermometer, of the air (or other medium and surroundings) in any particular place. The ambient temperature (e.g. an unheated room in winter) may be very different from an ideal ''room temperature''. Food and beverages may be served at "room temperature", meaning neither heated nor cooled. Comfort temperatures Comfort temperature is interchangeable with neutral temperature in the scientific literature, which can be calculated through regression analysis between thermal sensation votes and indoor temperature. ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Isopropanol
Isopropyl alcohol (IUPAC name propan-2-ol and also called isopropanol or 2-propanol) is a colorless, flammable, organic compound with a pungent alcoholic odor. Isopropyl alcohol, an organic polar molecule, is miscible in water, ethanol, and chloroform, demonstrating its ability to dissolve a wide range of substances including ethyl cellulose, polyvinyl butyral, oils, alkaloids, and natural resins. Notably, it is not miscible with salt solutions and can be separated by adding sodium chloride in a process known as salting out. It forms an azeotrope with water, resulting in a boiling point of 80.37 °C and is characterized by its slightly bitter taste. Isopropyl alcohol becomes viscous at lower temperatures, freezing at −89.5 °C, and has significant ultraviolet-visible absorbance at 205 nm. Chemically, it can be oxidized to acetone or undergo various reactions to form compounds like isopropoxides or aluminium isopropoxide. As an isopropyl group linked ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diethylether
Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs to the ether class of organic compounds. It is a common solvent and was formerly used as a general anesthetic. Production Most diethyl ether is produced as a byproduct of the vapor-phase Hydration reaction, hydration of ethylene to make ethanol. This process uses solid-supported phosphoric acid Catalysis, catalysts and can be adjusted to make more ether if the need arises: Vapor-phase Dehydration reaction, dehydration of ethanol over some Aluminium oxide, alumina catalysts can give diethyl ether yields of up to 95%. : Diethyl ether can be prepared both in laboratories and on an industrial scale by the acid ether synthesis. Uses The dominant use of diethyl ether is as a solvent. One particular application is in the production of cell ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Tin(IV) Chloride
Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound of tin and chlorine with the formula SnCl4. It is a colorless hygroscopic liquid, which fumes on contact with air. It is used as a precursor to other tin compounds. It was first discovered by Andreas Libavius (1550–1616) and was known as ''spiritus fumans libavii''. Preparation It is prepared from reaction of chlorine gas with tin at : : Structure Anhydrous tin(IV) chloride solidifies at −33 °C to give monoclinic crystals with the P21/c space group. It is isostructural with SnBr4. The molecules adopt near-perfect tetrahedral symmetry with average Sn–Cl distances of 227.9(3) pm. Reactions Tin(IV) chloride is well known as a Lewis acid. Thus it forms hydrates. The pentahydrate SnCl4·5H2O was formerly known as butter of tin. These hydrates consist of ''cis''- nCl4(H2O)2molecules together with varying amounts of water of crystallization. The additional water molecules ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
