Identification of stable porphomethenes and porphodimethenes from the reaction of sterically hindered aldehydes with pyrrole

Mathias O. Senge, Steffen Runge, Marcus Speck, Karin Ruhlandt-Senge

Research output: Contribution to journalArticle

48 Scopus citations

Abstract

Use of pivalaldehyde in mixed acid-catalyzed condensations of an aryl aldehyde with pyrrole allows the isolation and structural characterization of stable porphomethenes (5,10,15,22-tetrahydroporphyrins) and porphodimethenes (both 5,10- and 5,15-diphydroporphyrins) as intermediates of porphyrin synthesis. Crystal structures reveal the importance of the absolute configuration at the sp3-hybridized centers for the oxidation and stability of these (bio)synthetic intermediates. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)8927-8932
Number of pages6
JournalTetrahedron
Volume56
Issue number45
DOIs
StatePublished - Nov 3 2000

Keywords

  • Hydroporphyrins
  • Porphodimethenes
  • Porphomethenes
  • Porphyrins and analogues
  • Pyrroles
  • Silver porphyrins
  • Steric effects

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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