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Pinacol
Pinacol is a white solid organic compound. It is a diol that has hydroxyl groups (-OH) on vicinal carbon atoms. Preparation It may be produced by the pinacol coupling reaction from acetone: Reactions As a vicinal-diol, it can rearrange to pinacolone by the pinacol rearrangement, e.g. by heating with sulfuric acid: Pinacol can be used with borane and boron trichloride to produce useful synthetic intermediates such as pinacolborane, bis(pinacolato)diboron,{{OrgSynth , collvol = 10 , collvolpages = 115 , year = 2004 , prep = v77p0176 , title = Bis(pinacolato)diboron , author1 = Tatsuo Ishiyama, author2= Miki Murata, author3=Taka-aki Ahiko, author4-link= Norio Miyaura, author4=Norio Miyaura and pinacolchloroborane. See also * Semipinacol rearrangement The semipinacol rearrangement is a rearrangement reaction in organic chemistry involving a heterosubstituted alcohol of the type R1R2(HO)C–C(X)R3R4. The hetero substituent can be a halogen (Cl, Br, I), a tosylate, a ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pinacol Coupling Of Acetone
Pinacol is a white solid organic compound. It is a diol that has hydroxyl groups (-OH) on vicinal carbon atoms. Preparation It may be produced by the pinacol coupling reaction from acetone: Reactions As a vicinal-diol, it can rearrange to pinacolone by the pinacol rearrangement, e.g. by heating with sulfuric acid: Pinacol can be used with borane and boron trichloride to produce useful synthetic intermediates such as pinacolborane, bis(pinacolato)diboron Bis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula CH3)4C2O2Bsub>2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B2pin2. It ...,{{OrgSynth , collvol = 10 , collvolpages = 115 , year = 2004 , prep = v77p0176 , title = Bis(pinacolato)diboron , author1 = Tatsuo Ishiyama, author2= Miki Murata, author3=Taka-aki Ahiko, author4-link= Norio Miyaura, author4=Norio Miyaura and pinacolchloroboran ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pinacolone
Pinacolone (3,3-dimethyl-2-butanone) is an important ketone in organic chemistry. It is a colorless liquid and has a slight peppermint- or camphor- odor. It is a precursor to triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin. The molecule is an unsymmetrical ketone. The α-methyl group can participate in condensation reactions. The carbonyl group can undergo the usual reactions (hydrogenation, reductive amination, etc.). It is a Schedule 3 compound under the Chemical Weapons Convention 1993, due to being related to pinacolyl alcohol, which is used in the production of soman. It is also a controlled export in Australia Group member states. Preparation Most famously, at least in the classroom, pinacolone arises by the pinacol rearrangement, which occurs by protonation of pinacol (2,3-dimethylbutane-2,3-diol). : Industrially pinacolone is made by the hydrolysis of 4,4,5-trimethyl-1,3-dioxane, which is the product of is ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pinacolone
Pinacolone (3,3-dimethyl-2-butanone) is an important ketone in organic chemistry. It is a colorless liquid and has a slight peppermint- or camphor- odor. It is a precursor to triazolylpinacolone in the synthesis of the fungicide triadimefon and in synthesis of the herbicide metribuzin. The molecule is an unsymmetrical ketone. The α-methyl group can participate in condensation reactions. The carbonyl group can undergo the usual reactions (hydrogenation, reductive amination, etc.). It is a Schedule 3 compound under the Chemical Weapons Convention 1993, due to being related to pinacolyl alcohol, which is used in the production of soman. It is also a controlled export in Australia Group member states. Preparation Most famously, at least in the classroom, pinacolone arises by the pinacol rearrangement, which occurs by protonation of pinacol (2,3-dimethylbutane-2,3-diol). : Industrially pinacolone is made by the hydrolysis of 4,4,5-trimethyl-1,3-dioxane, which is the product of is ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pinacol Coupling Reaction
A pinacol coupling reaction is an organic reaction in which a carbon–carbon bond is formed between the carbonyl groups of an aldehyde or a ketone in presence of an electron donor in a free radical process. The reaction product is a vicinal diol. The reaction is named after pinacol (also known as 2,3-dimethyl-2,3-butanediol or tetramethylethylene glycol), which is the product of this reaction when done with acetone as reagent. The reaction is usually a homocoupling but intramolecular cross-coupling reactions are also possible. Pinacol was discovered by Wilhelm Rudolph Fittig in 1859. Reaction mechanism The first step in the reaction mechanism is a one-electron reduction of the carbonyl group by a reducing agent —such as magnesium— to a ketyl radical anion species. Two ketyl groups react in a coupling reaction yielding a vicinal diol with both hydroxyl groups deprotonated. Addition of water or another proton donor gives the diol. With magnesium as an electron donor, the initial ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pinacolborane
Pinacolborane is the borane with the formula (CH3)4C2O2BH. Often pinacolborane is abbreviated HBpin. It features a boron hydride functional group incorporated in a five-membered C2O2B ring. Like related boron alkoxides, pinacolborane is monomeric. It is a colorless liquid. It features a reactive B-H functional group. Use in organic synthesis In the presence of catalysts, pinacolborane hydroborates alkenes and, less rapidly, alkynes. Pinacolborane also affects catalyst-free hydroboration of aldehydes, ketones, and carboxylic acids. Pinacolborane is used in borylation, a form of C-H activation. Dehydrogenation of pinacolborane affords dipinacolatodiborane (B2pin2): :2{{nbsp(CH3)4C2O2BH → (CH3)4C2O2B-BO2C2(CH3)4 + H2 Related compounds *Catecholborane Catecholborane (abbreviated HBcat) is an organoboron compound that is useful in organic synthesis. This colourless liquid is a derivative of catechol and a borane, having the formula C6H4O2BH. Synthesis and structure Traditio ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Pinacol Rearrangement
The pinacol–pinacolone rearrangement is a method for converting a 1,2-diol to a carbonyl compound in organic chemistry. The 1,2-rearrangement takes place under acidic conditions. The name of the rearrangement reaction comes from the rearrangement of pinacol to pinacolone. : This reaction was first described by Wilhelm Rudolph Fittig in 1860 of the famed Fittig reaction involving coupling of 2 aryl halides in presence of sodium metal in dry ethereal solution. Mechanism In the course of this organic reaction, protonation of one of the –OH groups occurs and a carbocation is formed. If the –OH groups are not alike (i.e. the pinacol is asymmetrical), then the one which creates a more stable carbocation participates in the reaction. Subsequently, an alkyl group from the adjacent carbon migrates to the carbocation center. The driving force for this rearrangement step is believed to be the relative stability of the resultant oxonium ion. Although the initial carbocation is already ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Bis(pinacolato)diboron
Bis(pinacolato)diboron is a covalent compound containing two boron atoms and two pinacolato ligands. It has the formula CH3)4C2O2Bsub>2; the pinacol groups are sometimes abbreviated as "pin", so the structure is sometimes represented as B2pin2. It is a colourless solid that is soluble in organic solvents. It is a commercially available reagent for making pinacol boronic esters for organic synthesis. Unlike some other diboron compounds, B2pin2 is not moisture-sensitive and can be handled in air. Preparation and structure This compound may be prepared by treating tetrakis(dimethylamino)diboron with pinacol Pinacol is a white solid organic compound. It is a diol that has hydroxyl groups (-OH) on vicinal carbon atoms. Preparation It may be produced by the pinacol coupling reaction from acetone: Reactions As a vicinal-diol, it can rearrange t ... in acidic conditions. The B-B bond length is 1.711(6) Å. Dehydrogenation of pinacolborane provides an alternative route: :2(CH ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Diol
A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified. The most common industrial diol is ethylene glycol. Examples of diols in which the hydroxyl functional groups are more widely separated include 1,4-butanediol and propylene-1,3-diol, or beta propylene glycol, . Synthesis of classes of diols Geminal diols A geminal diol has two hydroxyl groups bonded to the same atom. These species arise by hydration of the carbonyl compounds. The hydration is usually unfavorable, but a notable exception is formaldehyde which, in water, exists in equilibrium with methanediol H2C(OH)2. Another example is (F3C)2C(OH)2, the hydrated form of hexafluoroacetone. Many gem-diols undergo further condensation to give dimeric and oligomeric derivatives. This reaction applies to glyoxal and related aldehydes. Vicinal diols In a vicinal diol, t ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Hydroxyl Groups
In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy groups. Both the negatively charged anion , called hydroxide, and the neutral radical , known as the hydroxyl radical, consist of an unbonded hydroxy group. According to IUPAC definitions, the term ''hydroxyl'' refers to the hydroxyl radical () only, while the functional group is called a ''hydroxy group''. Properties Water, alcohols, carboxylic acids, and many other hydroxy-containing compounds can be readily deprotonated due to a large difference between the electronegativity of oxygen (3.5) and that of hydrogen (2.1). Hydroxy-containing compounds engage in intermolecular hydrogen bonding increasing the electrostatic attraction between molecules and thus to higher boiling and melting points than found for compounds that lack this fu ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Vicinal (chemistry)
In chemistry the descriptor vicinal (from Latin ''vicinus'' = neighbor), abbreviated ''vic'', describes any two functional groups bonded to two adjacent carbon atoms (i.e., in a 1,2-relationship). Relation of atoms in a molecule For example, the molecule 2,3-dibromobutane carries two vicinal bromine atoms and 1,3-dibromobutane does not. Mostly, the use of the term vicinal is restricted to two ''identical'' functional groups. Likewise in a ''gem-''dibromide the prefix ''gem'', an abbreviation of geminal, signals that both bromine atoms are bonded to the ''same'' atom (i.e., in a 1,1-relationship). For example, 1,1-dibromobutane is geminal. While comparatively less common, the term hominal has been suggested as a descriptor for groups in a 1,3-relationship. Like other such descriptors as syn, anti, exo or endo, the description ''vicinal'' helps explain how different parts of a molecule are related to each other either structurally or spatially. The vicinal adjective is sometim ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Acetone
Acetone (2-propanone or dimethyl ketone), is an organic compound with the formula . It is the simplest and smallest ketone (). It is a colorless, highly volatile and flammable liquid with a characteristic pungent odour. Acetone is miscible with water and serves as an important organic solvent in its own right, in industry, home, and laboratory. About 6.7 million tonnes were produced worldwide in 2010, mainly for use as a solvent and production of methyl methacrylate (and from that PMMA) as well as bisphenol A.Acetone World Petrochemicals report, January 2010Stylianos Sifniades, Alan B. Levy, "Acetone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. It is a common building block in |
Sulfuric Acid
Sulfuric acid (American spelling and the preferred IUPAC name) or sulphuric acid ( Commonwealth spelling), known in antiquity as oil of vitriol, is a mineral acid composed of the elements sulfur, oxygen and hydrogen, with the molecular formula . It is a colorless, odorless and viscous liquid that is miscible with water. Pure sulfuric acid does not exist naturally on Earth due to its strong affinity to water vapor; it is hygroscopic and readily absorbs water vapor from the air. Concentrated sulfuric acid is highly corrosive towards other materials, from rocks to metals, since it is an oxidant with powerful dehydrating properties. Phosphorus pentoxide is a notable exception in that it is not dehydrated by sulfuric acid, but to the contrary dehydrates sulfuric acid to sulfur trioxide. Upon addition of sulfuric acid to water, a considerable amount of heat is released; thus the reverse procedure of adding water to the acid should not be performed since the heat released may boi ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
