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1,3-Cyclohexanedione is an organic compound with the formula (CH 2) 4 (CO) 2. It is one of three isomeric cyclohexanediones. It is a colorless compound that occurs naturally. It is the substrate for cyclohexanedione hydrolase. The compound exists mainly as the enol tautomer. [2]
Dimedone is an organic compound with the formula (CH 3) 2 C(CH 2) 2 (CO) 2 (CH 2). Classified as a cyclic diketone, it is a derivative of 1,3-cyclohexanedione. It is a white solid that is soluble in water, as well as ethanol and methanol. It once was used as a reagent to test for the aldehyde functional group.
Cyclic 1,3-diketones, such as 1,3-cyclohexanedione and dimedone, similarly exist significantly in the enol form. Like other diketones, 1,3-diketones are versatile precursors to heterocycles. The conjugate base derived from 1,3-ketones can serve as ligand s to form metal acetylacetonate coordination complexes.
A classic example for favoring the keto form can be seen in the equilibrium between vinyl alcohol and acetaldehyde (K = [enol]/[keto] ≈ 3 × 10 −7). In 1,3-diketones, such as acetylacetone (2,4-pentanedione), the enol form is favored. The acid-catalyzed conversion of an enol to the keto form proceeds by proton transfer from O to carbon.
The Wichterle reaction is a variant of the Robinson annulation that replaces methyl vinyl ketone with 1,3-dichloro-cis-2-butene. This gives an example of using a different Michael acceptor from the typical α,β-unsaturated ketone. The 1,3-dichloro-cis-2-butene is employed to avoid undesirable polymerization or condensation during the Michael ...
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