Oxidized forms of a tripyrrane: alpha-tripyrrinone, beta-tripyrrinone and a C-2 symmetric hexapyrrole

alpha- and beta-tripyrrinone isomers (3-6), and a C-2 symmetric hexapyrrole (7) were isolated from the oxidation of meso-perfluorophenyl tripyrrane 1 (and meso-2,6-dichlorophenyl tripyrrane 2) with DDQ under aerobic conditions, and the structure of 3 was determined by X-ray crystallographic analysis.