Models for non-heme oxidation enzymes

Pure and Applied Chemistry

Volumn 68, Issue 3, 1996, Pages 497-504

  Barton, D H R ^a   Taylor, D K ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000553544     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668030497     Document Type: Article

References (34)

1. Barton, D.H.R. and Doller, D. (1992) The Selective Functionalization of Saturated Hydrocarbons: Gif Chemistry, Acc. Chem. Res. 25, 504-512.
2. Balavoine, G., Barton, D.H.R., Boivin, J., Gref, A., Le Coupanec, P., Ozbalik, N., Pestana, J.A.X., and Riviere, H. (1988) Functionalisation of Saturated Hydrocarbons. Part X.1. A Comparative Study of Chemical and Electrochemical Processes (Gif and Gif-Orsay Systems) in Pyridine, in Acetone and in Pyridine-Co-Solvent Mixtures, Tetrahedron 44, 1091-1106.
3. Barton, D.H.R., Bévière, S.D., Chavasiri, W., Csuhai, E., Doller, D., and Liu, W.-G. (1992) The Functionalization of Saturated Hydrocarbons. Part 20. Alkyl Hydroperoxides: Reaction Intermediates in the Oxidation of Saturated Hydrocarbons by Gif-Type Reactions and Mechanistic Studies on Their Formation, J. Am. Chem. Soc. 114, 2147-2156.
4. Barton, D.H.R., Csuhai, E., and Doller, D. (1992) The Functionalization of Saturated Hydrocarbons. Part 23. Gif-type Bromination and Chlorination of Saturated Hydrocarbons: A Non-radical Reaction, Tetrahedron 48, 9195-9206.
5. Barton, D.H.R., Gastiger, M.J., and Motherwell, W.B. (1983) A New Procedure for the Oxidation of Saturated Hydrocarbons, J. Chem. Soc., Chem. Comm. 41-43.
6. Barton, D.H.R., Halley, F., Ozbalik, N., Schmitt, M., Young, E., and Balavoine, G. (1989) Functionalization of Saturated Hydrocarbons. 14. Further Studies on the Mechanism of Gif-Type Systems, J. Am. Chem. Soc. 111, 7144-7149.
7. Barton, D.H.R., Bévière, S.D., and Doller, D. (1991) An Unprecedented Chemical Transformation: the Oxidation of Alkanes to Alkyl Dimethyl Phosphates, Tetrahedron Lett. 32, 4671-4674.
8. Barton, D.H.R., Bévière, S.D., Chavasiri, W., Csuhai, E., and Doller, D. (1992) The Functionalization of Saturated Hydrocarbons. Part XXI. The Fe(III)-Catalyzed and the Cu(II)-Catalyzed Oxidation of Saturated Hydrocarbons by Hydrogen Peroxide: A Comparative Study, Tetrahedron 48, 2895-2910.
9. Barton, D.H.R., Bévière, S.D., Chavasiri, W., Doller, D., and Hu, B. (1992) The Fe(III)-Catalyzed Functionalization of Saturated Hydrocarbons by tert-Butyl Hydroperoxide: Mechanistic Studies on the Role of Dioxygen, Tetrahedron Lett. 33, 5473-5476.
10. V, Tetrahedron 50, 19-30.
11. IV Chemistry: The Formation of Carbon-Halogen Bonds, Tetrahedron 50, 31-46.
12. IV Chemistry: The Construction of C-N, C-S and C-C Bonds, Tetrahedron 50, 47-60.
13. V Conditions, Tetrahedron 50, 1011-1032.
14. Minisci, F. and Fontana, F. (1994) Mechanism of the Gif-Barton Type Alkane Functionalization by Halide and Pseudohalide Ions, Tetrahedron Lett. 35, 1427-1430.
15. Minisci, F., Fontana, F., Araneo, S., Recupeno, F. (1994) in press: Tetrahedron Lett..
16. Sheu, C., Sobkowiak, A., Zhang, L., Ozbalik, N., Barton, D.H.R., and Sawyer, D.T. (1989) Iron-Hydroperoxide Induced Phenylselenization of Hydrocarbons (Fenton Chemistry), J. Am. Chem. Soc. 111, 8030-8032.
17. 10(O)] and the Dioxygenation of Acetylenes and Arylolefins, J. Am. Chem. Soc. 112, 1936-1942.
18. 3) and the Monooxygenation (via PhNHNHPh) of Saturated Hydrocarbons: Reaction Mimic for the Methane Monooxygenase Proteins, J. Am. Chem. Soc. 112, 8212-8214.
19. Tung, H.-C., Kang, C., and Sawyer, D.T. (1992) Nature of the Reactive Intermediates from the Iron-Induced Activation of Hydrogen Peroxide: Agents for the Ketonization of Methylenic Carbons, the Monooxygenation of Hydrocarbons, and the Dioxygenation of Arylolefins, J. Am. Chem. Soc. 114, 3445-3455.
20. Schuchardt, U., Carvalho, W.A., Spinacé, E.V. (1993) Why is it Interesting to Study Cyclohexane Oxidation?, Synlett, 713-718.
21. II system in the Oxidation of Cyclohexane with Hydrogen Peroxide Under an Inert Atmosphere, New. J. Chem. 15, 955-958.
22. Briffaud, T., Larpent, C. and Patin, H. (1990) Catalytic Alkane Activations in Reverse Microemulsions Containing Iron Salts and Hydrogen Peroxide, J. Chem. Soc., Chem. Commun., 1193-1194.
23. Larpent, C. and Patin, H. (1992) Oxidation of alkanes with hydrogen peroxide catalyzed by iron salts or iron oxide colloids in reverse microemulsions, J. Mol. Catal. 72, 315-329.
24. II System, Tetrahedron Lett. 34, 5689-5692.
25. Barton, D.H.R., Bévière, S.D., Chavasiri, W., Doller, D., and Hu, B. (1993) New Alkane Functionalization Reactions Based on Gif-Type Chmeistry in the Presence of Alkali Metal Salts, Tetrahedron Lett. 34, 1871-1874.
26. Kruppa, G.H. and Beauchamp, J.L. (1986) Energetics and Structure of the 1- and 2-Adamantyl Radicals and Their Corresponding Carbonium Ions by Photoelectron Spectroscopy, J. Am. Chem. Soc. 108, 2162-2169; Walton, J.C. (1992) Bridgehead Radicals, Chem. Soc. Rev., 105-112; Tabuschi, I., Hamuro, J., and Oda, R. (1967) Free-Radical Substitution on Adamantane, J. Am. Chem. Soc. 89, 7127-7129.
27. Kruppa, G.H. and Beauchamp, J.L. (1986) Energetics and Structure of the 1- and 2-Adamantyl Radicals and Their Corresponding Carbonium Ions by Photoelectron Spectroscopy, J. Am. Chem. Soc. 108, 2162-2169; Walton, J.C. (1992) Bridgehead Radicals, Chem. Soc. Rev., 105-112; Tabuschi, I., Hamuro, J., and Oda, R. (1967) Free-Radical Substitution on Adamantane, J. Am. Chem. Soc. 89, 7127-7129.
28. Kruppa, G.H. and Beauchamp, J.L. (1986) Energetics and Structure of the 1- and 2-Adamantyl Radicals and Their Corresponding Carbonium Ions by Photoelectron Spectroscopy, J. Am. Chem. Soc. 108, 2162-2169; Walton, J.C. (1992) Bridgehead Radicals, Chem. Soc. Rev., 105-112; Tabuschi, I., Hamuro, J., and Oda, R. (1967) Free-Radical Substitution on Adamantane, J. Am. Chem. Soc. 89, 7127-7129.
29. Kochi, J.K. (1973) Free Radicals, John Wiley and Sons, Inc., New York.
30. +)] (1) as Hydroxylases (RH → ROH), not as Generators of Free Hydroxyl Radicals (HO'), J. Am. Chem. Soc. 115, 5817-5818 and references cited therein.
31. Yamazaki, I. and Piette, L.H. (1991) EPR Spin-Trapping Study on the Oxidizing Species Formed in the Reaction of the Ferrous Ion with Hydrogen Peroxide, J. Am. Chem. Soc. 113, 7588-7593.
32. Bartlett, P.D., Benzing, E.P., and Pincock, R.E. (1960) Peresters. V. Di-t-butylperoxyoxalate, J. Am. Chem. Soc. 82, 1762-1768.
33. Pryor, W.A., Fuller, D.L., and Stanley, J.P. (1972) Reactivity Patterns of the Methyl Radical, J. Am. Chem. Soc. 94, 1632-1638.
34. Clark, L.J. (1962) Iron (II) Determination in the Presence of Iron (III) Using 4,7-Diphenyl-1,10-phenanthroline, Anal. Chem. 34, 348-352.