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DOI: 10.1055/s-2005-861853
Electrophilic Nitration of meso-Tetraarylporphyrin Complexes at the β-Pyrrolic Position
Publication History
Publication Date:
09 March 2005 (online)
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Abstract
The selective nitration of meso-tetraphenylporphyrin complexes is described. The reaction of the above porphyrinates with 25% HNO3 or 5% HNO3 at room temperature or 0-5 °C, respectively, results in the formation of the corresponding mono β-nitroporphyrins (56-81%), accompanied by small amounts of a mixture of β,β-dinitro by-products. The results described above are the first known examples of β-mononitration of meso-tetraarylporphyrin complexes under electrophilic conditions. Reactions with nickel(II), copper(II), and cobalt(II) porphyrinates are discussed.
Key words
porphyrin complexes - electrophilic aromatic nitration - dimerization
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15Prepared directly before reaction by diluting fuming yellow nitric acid (d = 1.53).