13dikarbonyyliyhdisteissä

1,3-diketones, also known as beta-diketones, are organic compounds containing two carbonyl groups separated by a single methylene group. The general structure is R-CO-CH2-CO-R', where R and R' can be alkyl or aryl groups. The presence of the active methylene group between the two electron-withdrawing carbonyl groups makes the hydrogen atoms on this carbon acidic. This acidity allows 1,3-diketones to readily undergo tautomerization, existing in equilibrium between a diketo form and an enol form. The enol form is often stabilized by intramolecular hydrogen bonding.

This tautomerism is crucial to their reactivity. 1,3-diketones are versatile synthetic intermediates. They can act as nucleophiles due to the enolate ion formed by deprotonation of the active methylene group. This property allows them to participate in various carbon-carbon bond-forming reactions, such as alkylations and acylations. They are also important ligands in coordination chemistry, readily forming stable chelates with metal ions, often referred to as metal acetylacetonates. These metal complexes find applications as catalysts, in material science, and as precursors for thin film deposition. The synthesis of 1,3-diketones commonly involves the Claisen condensation or related reactions.