Synthesis of sterically congested unsymmetrical 1,2-dicarbonyl radicals through a stepwise approach.

A simplified and stepwise synthetic method for producing sterically congested unsymmetrical 1,2-dicarbonyl radicals was successfully demonstrated including detailed characterization of each radical cation. Using this approach, an aryl- and N-heterocyclic carbene-substituted 1,2-dicarbonyl radical in its neutral form is generated, revealing the stabilizing role of N-heterocyclic carbenes.