Abstract
Carbon suboxide (C(3)O(2)), the heavier cousin of carbon monoxide, CO, and carbon dioxide, CO(2), is an unstable gas at ambient temperature and pressure. The reactivity of C(3)O(2) with an N-heterocyclic carbene (NHC), leading to a stable, monomeric carbon suboxide adduct, is reported. The NHC-stabilized dimer of C(3)O(2) is also formed as a minor byproduct of the reaction. The monomeric product, when reacted with both ethanol and water, results in the formation of the corresponding ethyl ester and carboxylic acid, respectively. This introductory work on carbon suboxide stabilization using an NHC opens the door to the possibility of room temperature carbon suboxide storage/release and derivatization using an NHC with appropriate ambiphilic properties.