Ketonic decarboxylation

[2] This reaction is different from oxidative decarboxylation, which proceeds through a radical mechanism and is characterised by a different product distribution in isotopic labeling experiments with two different carboxylic acids.

The dry distillation of calcium acetate to give acetone was reported by Charles Friedel in 1858[3] and until World War I ketonization was the premier commercial method for its production.

[4] Ketonic decarboxylation of propanoic acid over a manganese(II) oxide catalyst in a tube furnace affords 3-pentanone.

[9] Of commercial interest are related ketonizations using cerium(IV) oxide and manganese dioxide on alumina as the catalysts.

[11] It was the first direct route cyclic compounds with more than 8 members and was used by Ružička to produce macrocyclic molecules with up to 34 carbon atoms.

[12] A more conventional example of intramolecular ketonization is the conversion of adipic acid to cyclopentanone with barium hydroxide.