Unusual reactivity of trifluoromethyl groups in meso-tetrakis(trifluoromethyl)porphyrin

Anikó Nemes, Egmont Mérész, István Jalsovszky, D. Szabó, Zsolt Böcskei, J. Rábai

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Based on the unusual reactivity of trifluoromethyl groups in nitrogen containing heterocycles, we synthesized the appropriate porphyrin mono-, di-, tri- or tetra-carboxylic ester derivatives by treatment of the precursor meso-tetrakis(trifluoromethyl)porphyrin with an excess of sodium- or potassium alkoxide in the respective alcohol. This method offers an efficient route for the synthesis of lower symmetry meso-substituted porphyrins compared to usual preparations utilizing stepwise condensation reactions. The structure of tetrakis(butyloxycarbonyl)porphyrin 5 was determined by X-ray analysis.

Original languageEnglish
Pages (from-to)75-80
Number of pages6
JournalJournal of Fluorine Chemistry
Volume203
DOIs
Publication statusPublished - Nov 1 2017

Keywords

  • Ester formation
  • Porphyrin
  • Solvolysis
  • Trifluoromethyl group
  • X-ray structure

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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