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A reaction kinetic study on the Gif-type biomimetic oxidation of cyclohexane

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Abstract

Kinetics of the oxidation of cyclohexane under Gif type conditions have been studied. A kinetic model is proposed, which is in agreement with the experimental results obtained. The rate equation showed the first order with respect to cyclohexane. A temperature dependence study of the reaction rate affords an activation energy of 14.3 kcal/mol.

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References

  • About-Jaudet, E., Barton, D. H. R., Csuhai, E. and Ozbalik, N., “The Effects of Ligand Variation on the Rate of Cyclododecane Oxidation under Modified GoAgg Conditions”,Tetrahedron Lett. 31, 1657 (1990).

    Article  CAS  Google Scholar 

  • Amatsu, H., Miyamoto, T. K. and Sasaki, Y., “Olefin Epoxidation Catalyzed by Sterically Bulky Metalloporphyrins by Use of Sodium Hypochlorite as an Oxygen Source”,Bull. Chem. Soc Jpn. 31, 3193 (1988).

    Article  Google Scholar 

  • Archakov, A. I. and Bachmanopva, G. I., “Cytochrome P-450 and Active Oxygen”, Taylor & Erancis: London, 1990.

    Google Scholar 

  • Balch, A. L., Lamar, G. N., Latos-Grazynski, L., Renner, M. W. and Thanabal, V., “Nuclear Magnetic Resonance Studies of Axial Aniline Coordination in Synthetic Ferryl, (FeNO)2, Porphyrin Complexes and in Ferryl Myglobin”,J. Am. Chem. Soc.,107, 3003 (1985).

    Article  CAS  Google Scholar 

  • Barton, D. H. R., Biviere, S. D., Chavasiri, W., Csuhai, E. and Doller, D., “The Functionalization of Saturated Hydrocarbons”,J. Am. Chem. Soc,114, 2147 (1992).

    Article  CAS  Google Scholar 

  • Barton, D. H. R., Gastiger, M. J. and Motherwell, W. B., “A New Procedure for the Oxidation of Saturated Hydrocarbons”,J. Chem. Soc Chem. Soc., Chem. Commun. 41, 731 (1983).

    Article  Google Scholar 

  • Barton, D. H. R., Lee, K. W., Mehr, W., Ozbalik, N. and Zhang, L., “Functionalization of Saturated Hydrocarbons”,Tetrahedron. 46, 3753 (1990).

    Article  CAS  Google Scholar 

  • Chin, D. H., Balch, A. L. and LaMar, G. M., “Formation of Porphin Ferry;(FeO2+) Complexes through the Addition of Nitrogen Bases to Peroxo-bridged Iron(III) Porphyrins”,J. Am. Chem. Soc. 102, 1446 (1980).

    Article  CAS  Google Scholar 

  • Collman, J. P., Brauman, J. I., Meunier, B., Hayashi, T., Kodadek, T. and Raybuck, S. A., “Epoxidation of Olefirs by Cytochrome P-450 Model Compounds”,J. Am. Chem. Soc.,107, 2000 (1985).

    Article  CAS  Google Scholar 

  • Dicken, C. M., Woon, T. C. and Bruice, T. C., “Kinetics and Mechanism of Oxygen Transfer in the Reaction of p-cyano-N,N-dimethyl Aniline N-oxide with Metaloporphyrin in Salts”,J. Am. Chem. Soc.,108, 1636 (1986).

    Article  CAS  Google Scholar 

  • Groves, J. T., Nemo, T. E. and Meyers, R. S., “Hydroxylation and Epoxidation Catalyzed by Iron-porphine Complexes”,J. Am. Chem. Soc.,101, 1032 (1979).

    Article  CAS  Google Scholar 

  • Lee, K. Y., Kim, S. B., Kim, Y. J. and Hong, S. I., “The Effect of Iron Catalysts on the Formation of Alcohol and Ketone in the Biomimetic Oxidation of Cyclohexane”,Bull. Korean Chem. Soc,15, 424 (1994).

    Google Scholar 

  • Mansuy, D., Bartoli, J. F. and Momenteau, M., “Alkane Hydroxylation Catalyzed by Metalloporphyrins”,Tetrahedron Lett.,23, 2781 (1982).

    Article  CAS  Google Scholar 

  • Nolte, R. J. M., Razenberg, J. A. S. J. and Schurman, R., “On the Rate-determining Step in the Epoxidation of Olefins by Mono-oxygenase”,J. Am. Chem. Soc,108, 2751 (1986).

    Article  CAS  Google Scholar 

  • Ojima, R., Kobayashi, N. and Osa, T., “Catalytic Epoxidation of Cyclooctene with Oxygen Using Electrochemically Reduced Metalloporphyrins”,Bull. Chem. Soc. Jpn.,63, 1374 (1990).

    Article  CAS  Google Scholar 

  • Sugimoto, H., Tung, H. C. and Saywer, D. T., “Formation, Characterization and Reactivity of Oxene Adduct of [Tetrakis (2,6-di-chlorophenyl) Porphinato]iron(HI) Perchlorate in Acetonitrile,J. Am. Chem. Soc.,110, 2465 (1988).

    Article  CAS  Google Scholar 

  • Traylor, T. G. and Miksatal, A. R., “Mechanism of Hemine-catalyzed Epoxidations”,J. Am. Chem. Soc.,109, 2770 (1981).

    Article  Google Scholar 

  • Traylor, T. G. and Xu, F., “Model Reactions Related to Cytochrome P-450”,J. Am. Chem. Soc,10, 1953 (1988).

    Article  Google Scholar 

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Kim, SB., Lee, KW. A reaction kinetic study on the Gif-type biomimetic oxidation of cyclohexane. Korean J. Chem. Eng. 12, 188–192 (1995). https://doi.org/10.1007/BF02705645

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  • DOI: https://doi.org/10.1007/BF02705645

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