Oxygenation of a dipyrromethene model for bilirubin: formation of a singlet oxygen-like product.

An oxodipyrromethene model compound for bilirubin is found to undergo oxidation to a blue tetrapyrrole and a water-propentdyopent on a silica gel thin layer chromatography plate. The reaction involves ground state oxygen and requires silica gel, although the propentdyopent is an expected product from reaction with singlet oxygen.