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

Fingerprint

porphyrin
Porphyrins
porphyrins
reactivity
Condensation reactions
X ray analysis
alkoxides
X-ray spectroscopy
ester
symmetry
condensation
esters
alcohol
potassium
Potassium
Esters
alcohols
Nitrogen
Sodium
routes

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

Cite this

Unusual reactivity of trifluoromethyl groups in meso-tetrakis(trifluoromethyl)porphyrin. / Nemes, Anikó; Mérész, Egmont; Jalsovszky, István; Szabó, D.; Böcskei, Zsolt; Rábai, J.

In: Journal of Fluorine Chemistry, Vol. 203, 01.11.2017, p. 75-80.

Research output: Contribution to journalArticle

Nemes, Anikó ; Mérész, Egmont ; Jalsovszky, István ; Szabó, D. ; Böcskei, Zsolt ; Rábai, J. / Unusual reactivity of trifluoromethyl groups in meso-tetrakis(trifluoromethyl)porphyrin. In: Journal of Fluorine Chemistry. 2017 ; Vol. 203. pp. 75-80.
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AU - Szabó, D.

AU - Böcskei, Zsolt

AU - Rábai, J.

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