Abstract
The π-extended flavonol Flav-1 (1) undergoes reaction with KOH or KO(2) to form 1(-), which reacts with O(2) at ambient temperature, resulting in CO release and depside formation. Mechanistic and DFT studies support a reaction pathway involving reaction of 1(-) with O(2) on the triplet energy surface in the rate-determining step. Formation of a cyclic peroxide leads to CO extrusion. These studies indicate that if formed in biological environments, 1(-) will release CO in the absence of light illumination.