An Efficient Aerobic Oxidation of Isobutane to t-Butyl Alcohol by N-Hydroxyphthalimide Combined with Co(II) Species

Bulletin of the Chemical Society of Japan

Volumn 71, Issue 5, 1998, Pages 1237-1240

  Sakaguchi, Satoshi ^a   Kato, Susumu ^a   Iwahama, Takahiro ^a   Ishii, Yasutaka ^a  

^a Fac Eng High Technol Res Ctr   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000203667     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.71.1237     Document Type: Article

References (57)

1. a) G. V. Nizova, G. Süss-Fink, and G. B. Shu;'pin, Tetrahedron, 53, 3603 (1977);
2. b) M. Lin, T. E. Hogan, and A. Sen, J. Am. Chem. Soc., 118, 4574 (1996);
3. c) M. Lin and A. Sen, Nature, 368, 613 (1994);
4. d) R. A. Sheldon, CHEMTECH, 24, 38 (1994);
5. e) D. H. R. Barton, A. E. Martell, and D. T. Sawyer, "The Activation of Dioxygen and Homogeneous Catalytic Oxidation," Plenum Press, New York (1993);
6. f) R. A. Sheldon, CHEMTECH, 21, 566 (1991);
7. g) C. L. Hill, "Activation and Functionalisation of Alkanes," Academic Press, New York (1989).
8. A representative review is shown in: "Kirk-Othmer Encyclopedia of Chemical Technology," 4th ed, ed by J. I. Kroschwitz and M. Howe-Grant, John Wiley and Sons, New York (1990), Vol. 4. See the following sections: a) E. Billig, Vol. 4, pp. 691-700; b) H.-D. Hahn, G. Dämbkes, and N. Rupprich, Vol. A4, pp. 463-474; c) C. E. Loeffler, L. Stautzenberber, and J. D. Unrun, Vol. A4, pp. 358-405, and references cited therein.
9. A representative review is shown in: "Kirk-Othmer Encyclopedia of Chemical Technology," 4th ed, ed by J. I. Kroschwitz and M. Howe-Grant, John Wiley and Sons, New York (1990), Vol. 4. See the following sections: a) E. Billig, Vol. 4, pp. 691-700; b) H.-D. Hahn, G. Dämbkes, and N. Rupprich, Vol. A4, pp. 463-474; c) C. E. Loeffler, L. Stautzenberber, and J. D. Unrun, Vol. A4, pp. 358-405, and references cited therein.
10. A representative review is shown in: "Kirk-Othmer Encyclopedia of Chemical Technology," 4th ed, ed by J. I. Kroschwitz and M. Howe-Grant, John Wiley and Sons, New York (1990), Vol. 4. See the following sections: a) E. Billig, Vol. 4, pp. 691-700; b) H.-D. Hahn, G. Dämbkes, and N. Rupprich, Vol. A4, pp. 463-474; c) C. E. Loeffler, L. Stautzenberber, and J. D. Unrun, Vol. A4, pp. 358-405, and references cited therein.
11. A representative review is shown in: "Kirk-Othmer Encyclopedia of Chemical Technology," 4th ed, ed by J. I. Kroschwitz and M. Howe-Grant, John Wiley and Sons, New York (1990), Vol. 4. See the following sections: a) E. Billig, Vol. 4, pp. 691-700; b) H.-D. Hahn, G. Dämbkes, and N. Rupprich, Vol. A4, pp. 463-474; c) C. E. Loeffler, L. Stautzenberber, and J. D. Unrun, Vol. A4, pp. 358-405, and references cited therein.
12. D. E. Winlker and G. W. Hearne, Ind. Eng. Chem., 53, 655 (1961).
13. a) B. M. Meunier, Chem. Rev., 92, 1411 (1992);
14. b) J. T. Groves and R. Neumann, J. Org. Chem., 53, 3891 (1988);
15. c) P. Battioni, J. F. Bartoli, P. Leduc, M. Fontecave, and D. Mansuy, J. Chem. Soc., Chem. Commun., 1987, 791;
16. d) E. I. Karasevich, A. M. Khenkin, and A. E. Shilov, J. Chem. Soc., Chem. Commun., 1987, 731;
17. e) D. H. R. Barton, J. Boivin, M. Gastiger, J. Morzycki, R. S. Huy-Motherwell, W. B. Motherwell, N. Ozbalik, and K. M. Schwartzentruber, J. Chem. Soc., Perkin Trans. 1, 1986, 947;
18. f) D. Mansuy, M. Fontecave, and J. F. Bartoli, J. Chem. Soc., Chem. Commun., 1983, 253;
19. g) I. Tabushi and A. Yazaki, J. Am. Chem. Soc., 103, 7371 (1981);
20. h) I. Tabushi and N. Koga, J. Am. Chem. Soc., 101, 6456 (1979).
21. a) N. Mizuno, M. Tateishi, T. Hirose, and M. Iwamoto, Chem. Lett., 1993, 2137;
22. b) S.-I. Murahashi, Y. Oda, and T. Naota, J. Am. Chem. Soc., 114, 7913 (1992).
23. S.-I. Murahashi, Y. Oda, T. Naota, and N. Komiya, J. Chem. Soc., Chem. Commun., 1993, 139.
24. a) I. Yamakana, T. Akimoto, K. Nakagaki, and K. Otsuka, J. Mol. Catal. A: Chem., 110, 119 (1996);
25. b) I. Yamanaka,T. Akimoto, and K. Otsuka, Chem. Lett., 1994, 1511.
26. T. Punniyamurthy, M. M. Reddy, S. J. S. Kalra, and J. Iqubal, Pure Appl. Chem., 68, 619 (1996).
27. M. Hamamoto, K. Nakayama, Y. Nishiyama, and Y. Ishii, J. Org. Own., 58, 6421 (1993).
28. a) F. Bedoui, S. Gutiérrez Granados, J. Devynck, and Bied-Charreton, New J. Chem., 15, 939 (1991);
29. b) P. Leduc, P. Battioni, J. F. Bartoli, and D. Mansuy, Tetrahedron Lett., 29, 205 (1988).
30. a) A. Maldotti, C. Bartocci, G. Varani, A. Molinari, P. Battioni, and D. Mansuy, Inorg. Chem., 35, 1126 (1996);
31. b) W.-D. Wang, A. Bakac, and J. H. Espenson, Inorg. Chem., 34, 6034 (1995);
32. c) A. Maldotti, C. Bartocci, R. Amadelli, E. Polo, P. Battioni, and D. Mansuy, J. Chem. Soc., Chem. Commun., 1991, 1487.
33. a) J. E. Lyons, P. E. Ellis, Jr., and H. K. Myers, J. Catal., 155, 59 (1995);
34. b) J. E. Lyons and P. E. Ellis, Jr., Catal. Lett., 8, 45 (1991);
35. c) P. E. Ellis, Jr., and J. E. Lyons, Coord. Chem. Rev., 105, 181 (1990);
36. d) P. E. Ellis, Jr., and J. E. Lyons, J. Chem. Sac., Chem. Commun., 1989, 1187;
37. e) P. E. Ellis, Jr., and J. E. Lyons, J. Chem. Soc., Chem. Commun., 1989, 1189;
38. f) P. E. Ellis, Jr., and J. E. Lyons, J. Chem. Soc., Chem. Commun., 1989, 1315;
39. g) P. E. Ellis, Jr., and J. E. Lyons, Catal. Lett., 3, 389 (1989).
40. a) J. F. Bartoli, P. Battioni, W. R. de Foor, and D. Mansuy, J. Chem. Soc., Chem, Commun., 1994, 23;
41. b) J. F. Bartoli, O. Brigaud, P. Battioni, and D. Mansuy, J. Chem. Soc., Chem. Commun., 1991, 440.
42. M. W. Grinstaff, M. G. Hill, J. A. Labinger, and H. B. Gray, Science, 264, 1311 (1994).
43. T. Wijesekera, J. E. Lyons, P. E. Ellis, Jr., and M. V. Bhinde, U.S. Patent 5608054 (126:199253h).
44. a) Y. Yoshino, Y. Hayashi, T. Iwahama, S. Sakaguchi, and Y. Ishii, J. Org. Chem., 62, 6810 (1997);
45. b) Y. Ishii, S. Kato, T. Iwahama, and S. Sakaguchi, Tetrahedron Lett., 37, 4993 (1996);
46. c) Y. Ishii, Y. Iwahama, S. Sakaguchi, K. Nakayama, and Y. Nishiyama, J. Org. Chem., 61, 4520 (1996);
47. d) Y. Ishii, K. Nakayama, M. Takeno, S. Sakaguchi, T. Iwahama, and Y. Nishiyama, J. Org. Chem., 60, 3934 (1995);
48. e) T. Iwahama, S. Sakaguchi, Y. Nishiyama, and Y. Ishii, Tetrahedron Lett., 36, 6923 (1995).
49. J. March, "Advanced Organic Chemistry," 4th ed, John Wiley and Sons, New York (1992), p. 1099.
50. E. C. Niederhoffer, J. H. Timmons, and A. E. Martell, Chem. Rev., 84, 137 (1984).
51. a) T. Yamada and T. Mukaiyama, Chem. Lett., 1989, 519, and references cited therein;
52. b) C. L. Wong, J. A. Switer, K. P. Balakrishnan, and J. F. Endicott, J. Am. Chem. Soc., 102, 5511 (1980);
53. c) R. S. Drago, J. P. Cannady, and K. A. Leslie, J. Am. Chem. Soc., 102, 6014 (1980).
54. 16a)
55. a) J. D. Bacha and J. K. Kochi, J. Org. Chem., 30, 3272 (1965);
56. b) F. D. Greene, M. L. Savitz, F. D. Osterholts, H. H. Fau, W. H. Smith, and P. M. Zanet, J. Org. Chem., 28, 55 (1963);
57. c) J. K. Kochi, J. Am. Chem. Soc., 84, 1193 (1962).