Direct Oxidations of meso -Tetrakis(pentafluorophenyl)porphyrin: Porphotrilactones and Entry into a Nonbiological Porphyrin Degradation Pathway.

The direct oxidations of meso -tetrakis(pentafluorophenyl)porphyrin using cetyltrimethylammonium permanganate (CTAP), RuCl 3 /Oxone/base or Ag + /oxalic acid each generate distinctive product mixtures that may contain, inter alia, porpho-mono-, di-, and trilactones. The CTAP and RuCl 3 /Oxone/base oxidations also generate a unique open chain tripyrrin derived from the degradation of a porpholactone oxazolone moiety. Thus, its formation and structure are distinctly different from all biological or nearly all other nonbiological biliverdin-like linear porphyrinoid degradation products that are derived from ring cleavages between the pyrrolic building blocks.