Acyloins
| Acyloins |
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| Structural formula of acyloins with the characteristic α-hydroxyketo group ( marked in blue ). The radicals R 1 and R 2 are organyl radicals ( alkyl radicals, aryl radicals, aklylaryl radicals, etc.); The hydrogen bond between the carbonyl oxygen atom and the hydrogen atom of the hydroxyl group is shown in dashed lines . |
Acyloins are a class of compounds in organic chemistry that have a keto group and a hydroxyl group on adjacent carbon atoms . So they are α - hydroxy ketones . Benzoins are a special form , in which both radicals R 1 and R 2 are aryl radicals (e.g. phenyl radicals ). Acyloins form intramolecular hydrogen bonds .
Acyloins are synthetically accessible through an acyloin condensation . Rubottom oxidation also offers the possibility of preparing acyloins from silyl ethers of enols . Aromatic acyloins can be represented by a benzoin addition .
In the alkaline environment, acyloins form enediolate anions which have a reducing effect (e.g. on Fehling's solution ) and are oxidized to 1,2- diketones in the process. Vicinal diols are obtained by reducing acyloins .
Individual evidence
- ↑ L. Kürti , B. Czakó: Stratigic Applications of Named Reactions in Organic Synthesis . Elsevier Academic Press, Amsterdam 2005 , ISBN 978-0-12-429785-2 , pp. 4-5.