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

Journal of the American Chemical Society

Volumn 114, Issue 6, 1992, Pages 2147-2156

  Barton, Derek H R ^a   Béviére, Stéphane ^a   Chavasiri, Warinthorn ^a   Csuhai, Eva ^a   Doller, Darío ^a   Liu, Wei Guo ^a  

^a TEXAS A AND M UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001298165     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00032a032     Document Type: Article

References (88)

1. Channa Reddy, C.; Hamilton, G. A.; Madyastha, K. M. In Biological Oxidation Systems; Academic Press: 1990; San Diego, California, Vol. I, pp xix-xx
2. Kurusu, Y.; Neckers, D. C. J. Org. Chem. 1991, 56, 1981-1983.
3. Kitajima, N.; Ito, M.; Fukui, H.; Moro-oka, Y. J. Chem. Soc., Chem. Commun. 1991, 102-104.
4. Briffaud, T.; Larpent, C.; Patin, H. J. Chem. Soc., Chem. Commun. 1990, 1193-1194.
5. Norman, R. E.; Yan, S.; Que, Jr., L.; Backes, G.; Ling, J.; Sanders-Loehr, J.; Zhang, J. H.; O'Connor, Ch. J. J. Am. Chem. Soc. 1990, 112, 1554-1562.
6. Traylor, T. G.; Xu, F. J. Am. Chem. Soc. 1990, 112, 178-186.
7. Sheu, C.; Sawyer, D. T. J. Am. Chem. Soc. 1990, 112, 8212-8213.
8. Borovik, A. S.; Hemdrich, M. P.; Holman, T. R.; Münck, E.; Papaefthymiou, V.; Que, Jr., L. J. Am. Chem. Soc. 1990, 112, 6031-6038.
9. Kitajima, N.; Fukui, H.; Moro-oka, Y. J. Chem. Soc., Chem. Commun. 1988, 485-486.
10. Gorum, S. M.; Papaefthymiou, G. C.; Frankel, R. B.; Lippard, S. J. J. Am. Chem. Soc. 1987, 109, 3337-3348.
11. Murch, B. P.; Bradley, F. C.; Que, Jr., L. J. Am. Chem. Soc. 1986, 108, 5027-5028.
12. Traylor, T. G.; Lee, W. A.; Stynes, D. V. J. Am. Chem. Soc. 1984, 106, 755-764.
13. Armstrong, W. H.; Lippard, S. J. J. Am. Chem. Soc. 1983, 105, 4837-4838
14. Barton, D. H. R.; Halley, F.; Ozbalik, N.; Schmitt, M.; Young, E.; Balavoine, G. J. Am. Chem. Soc. 1989, 111, 7144-7149.
15. Barton, D. H. R.; Ozbalik, N. Selective Functionalization of Saturated Hydrocarbons by the “Gif” and “Gif-Orsay” Systems. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; J. Wiley & Sons, Inc.: New York, 1989; Chapter IX, pp 281-301.
16. Barton, D. H. R.; Csuhai, E.; Ozbalik, N. Tetrahedron 1990, 46, 3743-3752
17. Barton, D. H. R.; Doller, D. The Selective Functionalization of Saturated Hydrocarbons. Gif and All That. In Dioxygen Activation and Homogeneous Catalytic Oxidation; Simándi, L. I., Ed.; Elsevier: Amsterdam, 1991; pp 1-10
18. Woodland, M. P.; Patil, D. S.; Cammack, R.; Dalton, H. Biochim. Biophys. Acta 1986, 873, 237-242
19. Ericson, A.; Hedman, B.; Hodgson, K. O.; Green, J.; Dalton, H.; Bentsen, J. G.; Beer, R. H.; Lippard, S. J. J. Am. Chem. Soc. 1988, 110, 2330-2332.
20. Fox, B. G.; Froland, W. A.; Dege, J.; Lipscomb, J. D. J. Biol. Chem. 1989, 264, 10023-10033.
21. Kivirikko, K. L.; Myllyla, R.; Pihlajaniemi, T. FASEB 1989, 3, 1609-1617.
22. Baldwin, J. E. J. Heterocycl. Chem. 1990, 27, 71-78.
23. Ziering, D. L.; Pascal, Jr., R. A. J. Am. Chem. Soc. 1990, 112, 834-838.
24. Suga, A.; Sugiyama, T.; Otsuka, M.; Ohno, M.; Sugiura, Y.; Maeda, K. Tetrahedron 1991, 47, 1191-1204
25. Kittaka, A.; Sugano, Y.; Otsuka, M.; Ohno, M. Tetrahedron 1988, 44, 2811-2820, 2821-2833
26. Stubbe, J.; Kozarich, J. W. Chem. Rev. 1987, 87, 1107-1136
27. Hecht, S. M. Acc. Chem. Res. 1986, 19, 383-390
28. Leising, R. A.; Brennan, B. A.; Que, Jr., L.; Fox, B. G.; Münck, E. J. Am. Chem. Soc. 1991, 113, 3988-3990
29. Likhtenshtein, G. I. Chemical Physics of Redox Metalloenzyme Catalysis·, Springer-Verlag: Berlin, 1988; Chapter VI, pp 123-160 and Chapter XI, pp 250-291
30. Bielski, B. H. J.; Thomas, M. J. J. Am. Chem. Soc. 1987, 109, 7761-7764
31. Kremer, M. L. Int. J. Chem. Kinet. 1985, 17, 1299-1314
32. Walling, C.; Goosen, A. J. Am. Chem. Soc. 1973, 95, 2987-2991
33. Nanthakumar, A.; Goff, H. M. J. Am. Chem. Soc. 1990, 112, 4047-4049
34. Levasen, W.; McAuliffe, C. A. Coord. Chem. Rev. 1974, 12, 151-184
35. Klemm, W. Angew. Chem. 1954, 16, 468-474
36. Walling, C.; Kurz, M.; Schugar, H. J. Inorg. Chem. 1970, 9, 931-937.
37. Barton, D. H. R.; Csuhai, E.; Doller, D.; Ozbalik, N.; Senglet, N. Tetrahedron Lett. 1990, 30, 3097-3100.
38. Balavoine, G.; Barton, D. H. R.; Boivin, J.; Lecoupanec, P.; Lelandais, P. New J. Chem. 1989, 13, 691-700.
39. Balavoine, G.; Barton, D. H. R.; Gref, A.; Lellouche, I. Tetrahedron Lett. 1991, 32, 2351-2354
40. Sugimoto, H.; Sawyer, D. T. J. Am. Chem. Soc. 1985, 107, 5712-5716
41. Sugimoto, H.; Sawyer, D. T. J. Org. Chem. 1985, 50, 1784-1786
42. Groves, J. T.; Van der Puy, M. J. Am. Chem. Soc. 1976, 98, 5290-5297.
43. Barton, D. H. R.; Csuhai, E.; Doller, D.; Balavoine, G. Proc. Natl. Acad. Sci. U.S.A. 1990, 87, 3401-3404.
44. Barton, D. H. R.; Csuhai, E.; Doller, D.; Balavoine, G. J. Chem. Soc., Chem. Commun. 1990, 1787-1789.
45. Barton, D. H. R.; Csuhai, E.; Ozbalik, N. Tetrahedron Lett. 1990, 31, 2817-2820.
46. About-Jaudet, E.; Barton, D. H. R.; Csuhai, E.; Ozbalik, N. Tetrahedron Lett. 1990, 31, 1657-1660
47. Franz, J. A.; Bushaw, B. A.; Alnajjar, M. S. J. Am. Chem. Soc. 1989, 111, 268-275.
48. Newcomb, M.; Manek, M. B. J. Am. Chem. Soc. 1990, 112, 9662-9663.
49. Barton, D. H. R.; Doller, D.; Geletii, Yu. V. Tetrahedron Lett. 1991, 32, 3811-3814
50. Fossey, J.; Lefort, D.; Massoudi, M.; Nedelec, J.-Y.; Sorba, J. Can. J. Chem. 1985, 63, 678-680.
51. Mantsch, H. H.; Saitô, H.; Smith, I. C. P. Prog. NMR Spectrosc. 1977, 11, 211-272.
52. Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. Tables of Spectral Data for Structure Determination of Organic Compounds, 2nd ed.; Springer-Verlag: Berlin, 1989; p C190.
53. Williams, H. R.; Mosher, H. S. J. Am. Chem. Soc. 1954, 76, 2984-2987
54. Barton, D. H. R.; Csuhai, E.; Dollar, D.; Geletii, Yu. V. Tetrahedron 1991, 47, 6561-6570
55. Negishi, E.-I. Organometallics in Organic Synthesis; Wiley: New York, 1980; Vol. 1, pp 76-77
56. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry; Harper & Row: New York, 1987; Chapter 8, pp 661-735.
57. Cooper, M. S.; Heaney, H.; Newbold, A. J.; Sanderson, W. R. Synlett. 1990, 533-535
58. Sweeley, C. C.; Bentley, R.; Makita, M.; Wells, W. W. J. Am. Chem. Soc. 1963, 85, 2497-2507
59. Knight, C.; Perkins, M. J. J. Chem. Soc., Chem. Commun. 1991, 925-927.
60. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 5687-5698.
61. Bowry, V. W.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1989, 111, 1927-1928
62. Chatteauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1988, 110, 2877-2885
63. Evans, C. A. Aldrichimica Acta 1979, 12, 23-29
64. Keana, J. F. W. Chem. Rev. 1978, 78, 37-64
65. Barton, D. H. R.; Bévière, S. D.; Doller, D. Tetrahedron Lett. 1991, 32, 4671-4674.
66. Kochi, J. K. Free Radicals; Wiley: New York, 1973; Chapter 11, p 625.
67. Ingold, K. U. Acc. Chem. Res. 1969, 2, 1-9.
68. Plumb, J. B.; Griffin, C. E. J. Org. Chem. 1963, 28, 2908-2910.
69. Buckler, S. A. J. Am. Chem. Soc. 1962, 84, 3093-3097
70. Walling, C.; Rabinowitz, R. J. Am. Chem. Soc. 1959, 81, 1243-1249.
71. Tishchenko, N. A.; Rudakov, E. S.; Volkova, L. K. Kinet. Ratal. 1989, 30, 319-325
72. Tishchenko, N. A.; Rudakov, E. S.; Lyubchik, S. B. Kinet. Ratal. 1989, 30, 588-593
73. Huyser, E. S.; Schimke, H.; Burham, R. L. J. Org. Chem. 1963, 28, 2141-2143.
74. Traynham, J. G.; Lee, Y.-S. J. Am. Chem. Soc. 1974, 96, 3590-3594
75. Saillard, J.-Y. Theoretical Aspects of Alkane C-H Activation by Organometallics. In Selective Hydrocarbon Activation; Davies, J. A., Watson, P. L, Greenberg, A.; Liebman, J. F., Eds.; VCH Publishers: New York, 1990; Chapter 7.
76. Arasasingham, R. D.; Balch, A. L.; Hart, R. L.; Latos-Grażyński, L. J. Am. Chem. Soc. 1990, 112, 7566-7571.
77. Balch, A. L.; Hart, R. L.; Latos-Grażyński, L. J. Am. Chem. Soc. 1990, 112, 7382-7388.
78. Arasasingham, R. D.; Balch, A. L.; Cornman, C. R.; Latos-Grażński, L. J. Am. Chem. Soc. 1989, 111, 4357-4363.
79. Arasasingham, R. D.; Balch, A. L.; Latos-Grażyński, L. J. Am. Chem. Soc. 1987, 109, 5846-5847.
80. Sheu, C.; Richert, S. A.; Cofré, P.; Ross, B., Jr.; Sobkowiak, A.; Sawyer, D. T.; Konofsky, J. R. J. Am. Chem. Soc. 1990, 112, 1936-1942.
81. Fish, R. H.; Konings, M. S.; Oberhausen, K. J.; Fong, R. H.; Yu, W. M.; Christou, G.; Vincent, J. B.; Coggin, D. K.; Buchanan, R. M. Inorg. Chem. 1991, 30, 3002-3006
82. Deighton, N.; Podmore, I. D.; Symons, M. C. R.; Wilkins, P. C.; Dalton, H. J. Chem. Soc., Chem. Commun. 1991, 1086.
83. Klagman, D. L.; Griffin, T. S. J. Am. Chem. Soc. 1973, 95, 197-199.
84. Reich, H. J.; Cohen, M. L. J. Org. Chem. 1979, 44, 3148-3151.
85. Geiss, F.; Blech, G. J. Labelled Compd. 1968, 4, 119-127.
86. Kabalka, G. W.; Baker, J. D.; Jr. J. Org. Chem. 1975, 40, 1834-1835.
87. Kovtun, G. A.; Aleksandrov, A. L.; Golubev, V. A. Izvest. Akad. Nauk 1974, 10, 2197-2204.
88. Barton, D. H. R. Aldrichimica Acta 1990, 23, 3-11