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

Nisansala Hewage; Dinusha Damunupola; Matthias Zeller; Christian Brückner

doi:10.1021/acs.joc.4c00283

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

J Org Chem. 2024 May 3;89(9):6584-6589. doi: 10.1021/acs.joc.4c00283. Epub 2024 Apr 23.

Authors

Nisansala Hewage¹, Dinusha Damunupola¹, Matthias Zeller², Christian Brückner¹

Affiliations

¹ Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
² Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, United States.

PMID: 38652047
DOI: 10.1021/acs.joc.4c00283

Abstract

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.