The porphyrin-bridged cyclophane 1 was prepared in order to mimic monooxygenase activity and serve as a supramolecular catalyst for the hydroxylation of polycyclic arenes. In methanol, arenes such as anthracene, ace-naphthylene, and phenanthrene are firmiy complexed in the nonpolar interior of 1. In 2,2,2-trifluoroethanol in the presence of iodobenzene, the iron(III) derivative 2 catalyzes the oxidation of acenaphthylene to ace-naphthen-1-one (65% yield).
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Benson et al. (1990) studied this question.
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