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Catalytic Cyclophanes: A Porphyrin‐Bridged Cyclophane as a Model for Cytochrome P‐450 Enzymes
Author(s) -
Benson David R.,
Valentekovich Robert,
Diederich François
Publication year - 1990
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199001911
Subject(s) - cyclophane , chemistry , porphyrin , anthracene , hydroxylation , cytochrome , perylene , catalysis , acenaphthylene , phenanthrene , stereochemistry , biocatalysis , supramolecular chemistry , photochemistry , organic chemistry , enzyme , crystal structure , reaction mechanism , molecule
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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