American Chemical Society
jo4c00283_si_002.pdf (3.56 MB)

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

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journal contribution
posted on 2024-04-23, 13:38 authored by Nisansala Hewage, Dinusha Damunupola, Matthias Zeller, Christian Brückner
The direct oxidations of meso-tetrakis­(penta­fluoro­phenyl)­porphyrin using cetyltrimethyl­ammonium permanganate (CTAP), RuCl3/Oxone/base or Ag+/oxalic acid each generate distinctive product mixtures that may contain, inter alia, porpho-mono-, di-, and trilactones. The CTAP and RuCl3/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.