Electrophillic bromination occurs regiospecifically at the antipodal pyrrolenic ring of free-base porphyrins bearing substituents that fix the aromatic delocalization pathway; this new feature of porphyrin chemistry is not observed in the reactions of the corresponding metalloporphyrins as the pre-requisite bond fixation is only possible in free-base compounds.
M. J. Crossley, P. L. Burn, S. S. Chew, F. B. Cuttance and I. A. Newsom, J. Chem. Soc., Chem. Commun., 1991, 1564 DOI: 10.1039/C39910001564
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