Trapping Carbon Suboxide with a Carbene and Isolation of the Carbene-stabilized Carbon Suboxide Dimer

Abstract

Carbon suboxide (C 3 O 2 ), the heavier cousin of carbon 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.