Acyloin condensation is a reductive coupling of two carboxylic esters using impure metallic sodium to yield an α-hydroxyketone, also known as an acyloin...
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In organic chemistry, acyloins or α-hydroxy ketones are a class of organic compounds of the general form R−C(=O)−CR'(OH)−R", composed of a hydroxy group...
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between aromatic aldehydes or glyoxals, and results in formation of an acyloin. In the classic example, benzaldehyde is converted to benzoin. The benzoin...
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succinate is a particularly versatile building block. It participates in acyloin condensation to give 2-hydroxycyclobutanone. Via condensation with oxalate...
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Semipinacol rearrangement (redirect from Acyloin rearrangement)
hydroxyketones and alpha hydroxy imines. Reactions of type 4 are also called acyloin rearrangements. While similar to the pinacol rearrangement, the semipinacol...
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nitriles. Pairs of esters are coupled to give α-hydroxyketones in the acyloin condensation As a class, esters serve as protecting groups for carboxylic...
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compounds with various aromas. As such it finds some use as a flavoring. Acyloin, the simplest secondary α-hydroxy ketone. Nodzu, Ryuzaburo (1935). "On...
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Normally such compounds are disfavored components in equilibria with acyloins. One special case is catechol, where the C=C subunit is part of an aromatic...
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or 1,4-butanediol, depending on conditions. Sebacoin, derived from the acyloin condensation of dimethyl sebacate, is hydrogenated to 1,2-cyclodecanediol...
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synthetically. They readily react with the neutral aldehyde to form an acyloin dimer. Hence, synthetic chemists have developed various acyl anion synthetic...
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n-hexyl radical attacked by oxygen). In one study the photolysis of an acyloin derivative in water in presence of hydrogen tetrachloroaurate (HAuCl4)...
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Conversion of dimethyl ester of sebacic acid to cyclodecanediol by acyloin condensation followed by hydrogenation using a copper chromite catalyst....
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a carboxylic acid. Other routes to vic-diols are the hydrogenation of acyloins and the pinacol coupling reaction. 1,3-Diols are often prepared industrially...
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Benzoin (organic compound) (category Acyloins)
Benzoin (/ˈbɛnzoʊ.ɪn/ or /-ɔɪn/) is an organic compound with the formula PhCH(OH)C(O)Ph. It is a hydroxy ketone attached to two phenyl groups. It appears...
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methylene blue. In the first step an acyloin of glucose is formed. The next step is a redox reaction of the acyloin with methylene blue in which the glucose...
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(January 1996). "Studies on the Synthesis of Aureolic Acid Antibiotics: Acyloin Glycosidation Studies". The Journal of Organic Chemistry. 61 (18): 6098–6099...
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this reaction step the alkene group is first oxidized to an intermediate acyloin by action of osmium(III) chloride, oxone (sacrificial catalyst) and sodium...
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elevated temperatures, while another uses acyloin condensation of the ethyl ester of pimelic acid the acyloin again followed by oxidation by bromine. An...
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and R−C(=O)−CH2−C(OH)−R' (beta). Alpha-hydroxy ketones are also called acyloins. They are commonly formed by condensation or reductive coupling of two...
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substituents (i.e., defined stereochemistry). These general reactions include: Acyloin condensation; Anodic oxidations; and the Dieckmann condensation as applied...
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that of hydride reagents. Another modification uses a sodium dispersion. Acyloin condensation – The reductive coupling of esters, using sodium, to yield...
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Hydroxynorketamine (category Acyloins)
Hydroxynorketamine (HNK), or 6-hydroxynorketamine, is a minor metabolite of the anesthetic, dissociative, and antidepressant drug ketamine. It is formed...
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of the reaction has been known to occur in many substrates bearing the acyloin functional group. The picture below shows the ring expansion of a cyclopentane...
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fragmentation to 7. With hydroxyl alpha protons present, oxidation to the acyloin competes. Trifluoroacetic acid is found to facilitate the overall reaction...
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Acid anhydride preparation reactions Acyl halides preparation reactions Acyloins preparation reactions Alcohols preparation reactions Aldehydes preparation...
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Acetalisation Acetoacetic ester condensation Achmatowicz reaction Acylation Acyloin condensation Adams' catalyst Adams decarboxylation Adkins catalyst Adkins–Peterson...
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Finn, John (1 August 1984). "Synthesis of α-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines". The Journal...
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cheaper oxidant. Alternatively, vicinal diols or their oxidized sequelae (acyloins or α-hydroxy acids) can be oxidized with cleavage to two aldehydes or an...
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intermediates, appearing in reactions such as the final reduction step of the acyloin condensation. Benzil semidione (Ph−C(−O−)=C(−O•)−Ph), synthesized by Auguste...
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medium-sized ring compounds with 8 to 12 members from dicarboxylic acid esters by acyloin condensation and explained their unusual chemical reactivity by a "nonclassical"...
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