Metal carbonyl 18-electron complexes is sometimes catalysed by catalytic amounts of oxidants, via electron-transfer. Metal carbonyls react with reducing agents such as metallic sodium or sodium amalgam to give carbonylmetalate (or carbonylate) anions: For iron pentacarbonyl, one obtains the tetracarbonylferrate with loss of CO: Mercury can insert into the metal-metal bonds of some polynuclear metal carbonyls: The CO ligand is often susceptible to attack by nucleophiles. For example, trimethylamine oxide and bistrimethylsilylamide convert CO ligands to CO and CN, respectively. In the "Hieber base reaction", hydroxide ion attacks the CO ligand to give a metallacarboxylic acid, followed by the release of carbon
Metal carbonyl is a reaction with high atom economy, especially if the reaction proceeds with high regioselectivity. Another important reaction catalyzed by metal carbonyls is the hydrocarboxylation. The example below is for the synthesis of acrylic acid and acrylic acid esters: Also the cyclization of acetylene to cyclooctatetraene uses metal carbonyl catalysts: In the Monsanto and Cativa processes, acetic acid is produced from methanol, carbon monoxide, and water using hydrogen iodide as well as rhodium and iridium carbonyl catalysts, respectively. Related carbonylation reactions afford acetic anhydride. Carbon monoxide-releasing molecules are metal carbonyl complexes that are being developed as potential drugs to release