Acyloin condensation is a reductive coupling of two carboxylic esters using impure metallic sodium to yield an α-hydroxyketone, also known as an acyloin...

In organic chemistry, acyloins or α-hydroxy ketones are a class of organic compounds of the general form R−C(O)CH(OH)−R', composed of a hydroxy group (−OH)...

aromatic aldehydes or glyoxals (OCH=CHO), and results in formation of an acyloin (−C(O)CH(OH)−). In the classic example, benzaldehyde is converted to benzoin...

succinate is a particularly versatile building block. It participates in acyloin condensation to give 2-hydroxycyclobutanone. Via condensation with oxalate...

hydroxyketones and alpha hydroxy imines. Reactions of type 4 are also called acyloin rearrangements. While similar to the pinacol rearrangement, the semipinacol...

compounds with various aromas. As such it finds some use as a flavoring. Acyloin, the simplest secondary α-hydroxy ketone. Nodzu, Ryuzaburo (1935). "On...

For example, diesters are cyclized in the Dieckmann condensation: The acyloin condensation can be deployed similarly. For larger rings (macrocyclizations)...

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...

pyrolysis. Pairs of esters are coupled to give α-hydroxyketones in the acyloin condensation As a class, esters serve as protecting groups for carboxylic...

synthetically. They readily react with the neutral aldehyde to form an acyloin dimer. Hence, synthetic chemists have developed various acyl anion synthetic...

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...

Conversion of dimethyl ester of sebacic acid to cyclodecanediol by acyloin condensation followed by hydrogenation using a copper chromite catalyst....

n-hexyl radical attacked by oxygen). In one study the photolysis of an acyloin derivative in water in presence of hydrogen tetrachloroaurate (HAuCl4)...

or 1,4-butanediol, depending on conditions. Sebacoin, derived from the acyloin condensation of dimethyl sebacate, is hydrogenated to 1,2-cyclodecanediol...

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...

elevated temperatures, while another uses acyloin condensation of the ethyl ester of pimelic acid the acyloin again followed by oxidation by bromine. An...

this reaction step the alkene group is first oxidized to an intermediate acyloin by action of osmium(III) chloride, oxone (sacrificial catalyst) and sodium...

Finn, John (1 August 1984). "Synthesis of α-hydroxycarbonyl compounds (acyloins): direct oxidation of enolates using 2-sulfonyloxaziridines". The Journal...

cheaper oxidant. Alternatively, vicinal diols or their oxidized sequelae (acyloins or α-hydroxy acids) can be oxidized with cleavage to two aldehydes or an...

(January 1996). "Studies on the Synthesis of Aureolic Acid Antibiotics: Acyloin Glycosidation Studies". The Journal of Organic Chemistry. 61 (18): 6098–6099...

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...

transformations that are enabled or enhanced intramolecularly. For example, the acyloin condensation of diesters almost uniquely produces 10-membered carbocycles...

and R−C(=O)−CH2−CH(OH)−R' (beta). Alpha-hydroxy ketones are also called acyloins. They are commonly formed by condensation or reductive coupling of two...

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"...

fragmentation to 7. With hydroxyl alpha protons present, oxidation to the acyloin competes. Trifluoroacetic acid is found to facilitate the overall reaction...

substituents (i.e., defined stereochemistry). These general reactions include: Acyloin condensation; Anodic oxidations; and the Dieckmann condensation as applied...

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...

that of hydride reagents. Another modification uses a sodium dispersion. Acyloin condensation – The reductive coupling of esters, using sodium, to yield...

Decarboxylase: A Molecular Modeling Study of Pyruvate Decarboxylation and Acyloin Formation". J. Am. Chem. Soc. 118 (8): 1867–1873. doi:10.1021/ja951830t...

Acid anhydride preparation reactions Acyl halides preparation reactions Acyloins preparation reactions Alcohols preparation reactions Aldehydes preparation...