The 15-tert-butyl-5-oxophlorin 1 forms a stable, neutral pi-radical sp
ecies 2, in high yield; the 13,17-bis-unsubstituted 5-oxophlorin analo
gue 5, under similar conditions, affords the 15-iso-5-oxophlorin 6 and
15-hydroxy compound 7 (both characterized by X-ray crystallography),
the latter demonstrating the trapping of the pi-radical by dioxygen.