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

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.