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Science 27 May 1994:
Vol. 264. no. 5163, pp. 1311 - 1313
DOI: 10.1126/science.8191283
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Articles

Science, Vol 264, Issue 5163, 1311-1313
Copyright © 1994 by American Association for the Advancement of Science

articles

Mechanism of catalytic oxygenation of alkanes by halogenated iron porphyrins

MW Grinstaff, MG Hill, JA Labinger, and HB Gray

Arthur Amos Noyes Laboratory, California Institute of Technology, Pasadena 91125.

Halogenation of an iron porphyrin causes severe saddling of the macrocyclic structure and a large positive shift in the iron(III)/(II) redox couple. Although pre-halogenated iron(II) porphyrins such as Fe(TFPPBr8) [H2TFPPBr8, beta-octabromo-tetrakis(pentafluorophenyl)-porphyrin] are relatively resistant to autoxidation, they rapidly reduce alkyl hydroperoxides. These and related reactivity studies suggest that catalysis of alkane oxygenation by Fe(TFPPBr8)Cl occurs through a radical-chain mechanism in which the radicals are generated by oxidation and reduction of alkyl hydroperoxides.


THIS ARTICLE HAS BEEN CITED BY OTHER ARTICLES:
High-Level Production of Porphyrins in Metabolically Engineered Escherichia coli: Systematic Extension of a Pathway Assembled from Overexpressed Genes Involved in Heme Biosynthesis.
S. J. Kwon, A. L. de Boer, R. Petri, and C. Schmidt-Dannert (2003)
Appl. Envir. Microbiol. 69, 4875-4883
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