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
Oxymercuration reaction called an oxymercuration–reduction reaction or oxymercuration–demercuration reaction. This reaction, which is almost always done in practice instead of oxymercuration, is treated at the conclusion of the article. Oxymercuration can be fully described in three steps(the whole process is sometimes called "deoxymercuration"), which is illustrated in stepwise fashion to the right. In the first step, the nucleophilic double bond attacks the mercury ion, ejecting an acetoxy group. The electron pair on the mercury ion in turn attacks a carbon on the double bond, forming a "mercuronium ion" in which the mercury atom bears a positive charge. The electrons in the highest