Thermal CO Release Reactivity of a π-Extended Flavonol Anion

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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.