2,3,7,8,12,13,17,18-octachloroporphyrin

Mathias O. Senge, Oliver Flögel, Karin Ruhlandt-Senge

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

Synthesis of 3,4-dichloropyrrole and reaction with formaldehyde and p-toluene sulfonic acid catalysis, followed by oxidation with Ag2O allows a low yield entry into 2,3,7,8,12,13,17,18-octachloroporphyrin. The extremely low solubility of the free base requires work-up in the presence of metallo acetates for in situ formation of metal complexes. Utilizing this method, zinc(II) and nickel(II) complexes of the title compound were prepared as the first examples of a novel porphyrin class bearing only β-halogeno substituents. In addition, the first crystal structure of a 3,4-dihalopyrrole, 3,4-dichloropyrrole, is reported.

Original languageEnglish (US)
Pages (from-to)503-506
Number of pages4
JournalJournal of Porphyrins and Phthalocyanines
Volume5
Issue number6
DOIs
StatePublished - Jan 1 2001

Keywords

  • 2,3-dichloropyrrole
  • Catalysis
  • Electronic effects
  • Halogenation
  • β-Substituted porphyrins

ASJC Scopus subject areas

  • Chemistry(all)

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