Catalytic Oxidation of Alkylbenzenes with Molecular Oxygen under Normal Pressure and Temperature by N-Hydroxyphthalimide Combined with Co(OAc)2

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6810-6813

  Yoshino, Yasushi ^a   Hayashi, Yoshiaki ^a   Iwahama, Takahiro ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a High Technology Research Center   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000061116     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9708147     Document Type: Article

References (51)

1. (a) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
2. (b) Hill, C. L. Activation and Functionalization of Alkanes; Academic Press: New York, 1989.
3. (c) Sheldon, R. A. CHEMTECH 1991, 21, 566.
4. (d) Simandi, L. Catalytic Activation of Dioxygen by Metal Complexes; Kluwer Academic Publisher: Boston, 1992.
5. (e) March, J. Advanced Organic Chemistry, 4th ed.; John Wiley & Sons: New York, 1992; pp 705-708.
6. (f) The Activation of Dioxygen and Homogeneous Catalytic Oxidation; Barton, D. H. R., Martell, A. E., Sawyer, D. T., Eds.; Plenum Press: New York, 1993.
7. (g) Haber, J. Catalysis of Organic Reaction; Kosak, J. R., Johnson, T. A., Eds.; Marcel Dekker, Inc.; New York, 1993; pp 151-168.
8. (f) Sheldon, R. A. CHEMTECH 1994, 24, 38.
9. (a) Emanuel, N. M.; Denisov E. T.; Mazius, Z. Z. The Oxidation of Hydrocarbons in Liquid Phase; Plenum Press: New York, 1967.
10. (b) Hucknall, D. J. Selective Oxidation of Hydrocarbons; Academic Press: New York, 1974.
11. (c) Tanaka, K. CHEMTECH 1974, 555.
12. (d) Pines, H. The Chemistry of Catalytic Hydrocarbon Conversion; Academic Press; New York, 1981.
13. (e) Parshall, G. W.; Ittel, S. D. Homogeous Catalysis, 2nd ed.; John Wiley and Sons: New York, 1992; pp 255-261.
14. (a) Toland, W. G. Ind. Eng. Chem. 1958, 50, 1386.
15. (b) Brill, W. F. Ind. Eng. Chem. 1960, 52, 837.
16. (c) Opgrande, J. L.; Dorbratz, C. J.; Brown, E. E.; Liang, J. C.; Conn, G. S.; With, J.; Sheltpn, F. J. Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Howe-Grant, M., Eds.; John Wiley and Sons: New York, 1990; pp 103-115.
17. (d) Active Oxygen in Chemistry; Foote, C. S., Valentine, J. S., Greenberg, A., Liebman, J. F., Eds.; Chapman & Hall: New York, 1995.
18. (a) Tabushi, I.; Koga, N. J. Am. Chem. Soc. 1979, 101, 6456.
19. (b) Tabushi, I.; Yazaki, A. J. Am. Chem. Soc. 1981, 103, 7371.
20. (c) Mansuy, D.; Fontecave, M.; Bartoli, J. F. J. Chem. Soc., Chem. Commun. 1983, 253.
21. (d) Barton, D. H. R.; Boivin, J.; Gastiger, M.; Morzycki, J.; Hay-Motherwell, R. S.; Motherwell, W. B.; Ozbalik, N.; Schwartzentruber, K. M. J. Chem. Soc., Perkin Trans. 1 1986, 947.
22. (e) Karasevich, E. I.; Khenkin, A. M.; Shilov, A. E. J. Chem. Soc., Chem. Commun. 1987, 731.
23. (f) Battioni, P.; Bartoli, J. F.; Leduc, P.; Fontecave, M.; Mansuy, D. J. Chem. Soc., Chem. Commun. 1987, 791.
24. (g) Groves, J. T.; Neumann, R. J. Org. Chem. 1988, 53, 3891.
25. (h) Meunier, B. M. Chem. Rev. 1992, 92, 1411.
26. (a) Murahashi, S.-I.; Oda, Y.; Naota, T. J. Am. Chem. Soc. 1992, 114, 7913.
27. (b) Murahashi, S.-I.; Oda, Y.; Naota, T.; Komiya, N. J. Chem. Soc., Chem. Commun. 1993, 139.
28. Mizuno, N. Tateishi, M.; Hirose, T.; Iwamoto, M. Chem. Lett. 1993, 2137.
29. Hamamoto, M.; Nakayama, K.; Nishiyama, Y.; Ishii, Y. J. Org. Chem. 1993, 58, 6421.
30. (a) Yamanaka, I.; Akimoto, T.; Otuska, K. Chem. Lett. 1994, 1514.
31. (b) Yamanaka, I.; Akimoto, T.; Nakagaki, K.; Otuska, K. Chem. Lett. 1994, 1717.
32. (c) Yamanaka, I.; Akimoto, T.; Nakagaki, K.; Otuska, K. J. Mol. Catal. A: Chem. 1996, 110, 119.
33. Punniyamurthy, M.; Reddy, M.; Kalra, S. J. S.; Iqubal, J. Pure Appl. Chem. 1996, 68, 619.
34. Mlonicka, T. J. Mol. Catal. 1986, 36, 205, and references cited therein.
35. (a) Ellis, P. E., Jr.; Lyons, J. E. J. Chem. Soc., Chem. Commun. 1989, 1187.
36. (b) Ellis, P. E., Jr.; Lyons, J. E. J. Chem. Soc., Chem. Commun. 1989, 1189.
37. (c) Ellis, P. E., Jr.; Lyons, J. E. J. Chem. Soc., Chem. Commun. 1989, 1315.
38. (d) Lyons, J. E.; Ellis, P. E., Jr.; Myers, H. K., Jr. J. Catal. 1995, 155, 59.
39. (a) Grinstaff, M. W.; Hill, M. G.; Labinger, J.; Gray, H. B. Science 1994, 264, 1311.
40. (b) Böttcher, A.; Grinstaff, M. W.; Labinger, J. A.; Gray, H. B. J. Mol. Catal. A: Chem. 1996, 113, 191.
41. (a) Ishii, Y.; Nakayama, K.; Takeno, M.; Sakaguchi, S.; Iwahama, T.; Nishiyama, Y. J. Org. Chem, 1995, 60, 3934.
42. (b) Ishii, Y.; Iwahama, T.; Sakaguchi, S.; Nakayama, K.; Nishiyama, Y. J. Org. Chem, 1996, 61, 4520.
43. (c) Ishii, Y.; Kato, S.; Iwahama, T.; Sakaguchi, S. Tetrahedron Lett. 1996, 37, 4993.
44. Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
45. (a) Basolo, F.; Jones, R. D.; Summerville, D. A. Chem. Rev. 1979, 79, 139.
46. (b) Wong, C. L.; Switer, J. A.; Balakrishnan, K. P.; Endicott, J. F. J. Am. Chem. Soc. 1980, 102, 5511.
47. (c) Drago, R. S.; Cannady, J. P.; Leslie, K. A. J. Am. Chem. Soc. 1980, 102, 6014.
48. (d) Niederhoffer, E. C.; Timmons, J. H.; Martell, A. E. Chem Rev. 1984, 84, 137.
49. (e) Bozell, J. J.; Hames, B. R.; Dimmel, D. R. J. Org. Chem. 1995, 60, 2398.
50. 13b
51. Onopchenko, A.; Schultz, A. J. G. J. Org. Chem. 1973, 38, 3729, and references cited therein.