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

Summary 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.The authors wish to thank the National Science Foundation for generous support of this work. We also thank Mr.Richard Gillespie and Ms.Elizabeth Irwin for running the high resolution mass spectra.