Diketone
A diketone or dione is a molecule containing two ketone groups. The simplest diketone is diacetyl, also known as 2,3-butanedione. Diacetyl, acetylacetone, and hexane-2,5-dione are examples of 1,2-, 1,3-, and 1,4-diketones, respectively. Dimedone is an example of a cyclic diketone.
An important member is biacetyl, CH3C(O)C(O)CH3. These compounds are often generated by dehydrogenation of the diols:
A distinctive feature of 1,2-diketones is the long C-C bond linking the carbonyl groups. This bond distance is about 1.54 Å, compared to 1.45 Å for the corresponding bond in 1,3-butadiene. The effect is attributed to repulsion between the partial positive charges of the carbonyl carbon atoms.
1,2-Diketones condense with many bifunctional nucleophiles, such as urea and thiourea to give heterocycles. Upon condensation with aromatic amines, they convert to the diketimine ligands.
An important member is acetylacetone, CH3C(O)CH2C(O)CH3. Acetylacetone is prepared industrially by the thermal rearrangement of isopropenylacetate.
Classically, 1,3-diketones are prepared by condensation of ketones with esters.
1,3-Diketones are prone to exist as enols because of conjugation of the enol or enolate with the other carbonyl group, and the stability gained in forming a six-membered ring, (hydrogen bonded in the case of the enol or containing the counter ion in the case of the enolate).
Like other diketones, 1,3-diketones are versatile precursors to heterocycles. Hydrazine, for example, condenses to give pyrazoles. The conjugate base derived from 1,3-ketones form coordination complexes. In the DeMayo reaction 1,3-diketones react with alkenes in a photochemical pericyclic reaction to form (substituted) 1,5-diketones.
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