Mechanism in polyoxometalate-catalyzed homogeneous hydrocarbon oxo transfer oxidation. The [Co4(H2O)2P2W18O 68]10-/p-Cyano-N,N-dimethylaniline N-oxide selective catalytic epoxidation system

Journal of the American Chemical Society

Volumn 118, Issue 20, 1996, Pages 4809-4816

  Zhang, Xuan ^a   Sasaki, Ken ^a   Hill, Craig L ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; STILBENE OXIDE;

ARTICLE; CATALYSIS; EPOXIDATION; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0029887435     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9536983     Document Type: Article

References (75)

1. Pope, M. T. Heteropoly and Isopoly Oxometalates; Springer-Verlag: Berlin, 1983.
2. Day, V. W.; Klemperer, W. G. Science 1985, 228, 533-541.
3. Pope, M. T.; Müller, A. Angew. Chem., Int. Ed. Engl. 1991, 50, 34-48.
4. Chen, Q.; Zubieta, J. Coord. Chem. Rev. 1992, 114, 107-167.
5. Saha, S. K.; Ali, M.; Banerjee, P. Coord. Chem. Rev. 1993, 122, 41-62.
6. Kozhevnikov, I. V. Russ. Chem. Rev. 1993, 62, 473-491.
7. Hill, C. L.; Prosser-McCartha, C. M. In Photosensitization and Photocatalysis Using Inorganic and Organometallic Complexes; Kalyanasundaram, K.; Grätzel, M., Eds.; Kluwer Academic Publishers: Dordrecht, The Netherlands, 1993; Vol. 14, Chapter 13, pp 307-330.
8. Hill, C. L.; Kim, G.-S.; Prosser-McCartha, C. M.; Judd, D. Mol. Eng. 1993, 3, 263-275.
9. Okuhara, T.; Misono, M. Yuki Gosei Kagaku Kyokaishi 1993, 51, 128-140.
10. Mizuno, N.; Misono, M. J. Mol. Catal. 1994, 86, 319-342.
11. Jansen, R. J. J.; Vanveldhuizen, H. M.; Schwegler, M. A.; Vanbekkum, H. Recl. Trav. Chim. Pays-Bas 1994, 113, 115-135.
12. Kozhevnikov, I. V. Catal. Rev.-Sci. Eng. 1995, 37, 311-352.
13. Maksimov, G. M. Usp. Khim. 1995, 64, 480-496.
14. Hill, C. L.; Prosser-McCartha, C. M. Coord. Chem. Rev. 1995, 143, 407-455.
15. Hill, C. L.; Brown, R. B., Jr. J. Am. Chem. Soc. 1986, 108, 536-538.
16. Rong, C.; Pope, M. T. J. Am. Chem. Soc. 1992, 114, 2932-2938.
17. Mansuy, D.; Bartoli, J.-F.; Battioni, P.; Lyon, D. K., Finke, R. G. J. Am. Chem. Soc. 1991, 113, 7222-7226.
18. Steckhan, E.; Kandzia, C. Synlett 1992, 139-140.
19. Bressan, M.; Morvillo, A.; Romanello, G. J. Mol Catal. 1992, 77, 283-288
20. Khenkin, A. M.; Duncan, D. C.; Hill, C. L. J. Am. Chem. Soc. In submission.
21. Khenkin, A. M.; Hill, C. L. Mendeleev Commun. 1993, 140-142.
22. Khenkin, A. M.; Hill, C. L. J. Am. Chem. Soc. 1993, 115, 8178-8186.
23. Toth, J. E.; Anson, F. C. J. Am. Chem. Soc. 1989, 111, 2444-2451.
24. Schwegler, M.; Floor, M.; van Bekkum, H. Tetrahedron Lett. 1988, 29, 823-826.
25. Neumann, R.; Gara, M. J. Am. Chem. Soc. 1995, 117, 5066-5074.
26. Neumann, R.; Khenkin, A. M.; Dahan, M. Angew. Chem., Int. Ed. Engl. 1995, 34, 1587-1589.
27. Neumann, R.; Dahan, M. J. Chem. Soc., Chem. Commun. 1995, 171-172.
28. Neumann, R.; Gara, M. J. Am. Chem. Soc. 1994, 116, 5509-5510.
29. Bart, J. C.; Anson, F. C. J. Electroanal. Chem. 1995, 390, 11-19.
30. Yang, Y.; Diederich, F.; Valentine, J. S. J. Am. Chem. Soc. 1990, 112, 7826-7828.
31. Smegal, J. A.; Schardt, B. C.; Hill, C. L. J. Am. Chem. Soc. 1983, 105, 3510-3515.
32. Smegal, J. A.; Hill, C. L. J. Am. Chem. Soc. 1983, 105, 3515-3521.
33. Schardt, B. C.; Hill. C. L. Inorg. Chem. 1983, 22, 1563-1565.
34. Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981; Chapter 3.
35. Hill, C. L.; Khenkin, A. M.; Weeks, M. S.; Hou, Y. In ACS Symposium Series on Catalytic Selective Oxidation; Oyama, S. T., High-tower, J. W., Eds.; American Chemical Society: Washington, DC, 1993; Chapter 6, pp 67-80.
36. Drago, R. S.; Beer, R. H. Inorg. Chim. Acta 1992, 200, 359-367.
37. Drago, R. S. Coord. Chem. Rev. 1992, 117, 185-213.
38. Dicken, C. M.; Lu, F.-L.; Nee, M. W.; Bruice, T. C. J. Am. Chem. Soc. 1985, 107, 5776-5789.
39. Yuan, L.-C.; Calderwood, T. S.; Bruice, T. C. J. Am. Chem. Soc. 1985, 107, 8273-8274.
40. Dicken, C. M.; Woon, T. C.; Bruice, T. C. J. Am. Chem. Soc. 1986, 108, 1636-1643.
41. Woon, T. C.; Dicken, C. M.; Bruice, T. C. J. Am. Chem. Soc. 1986, 108, 7990-7995.
42. Dicken, C. M.; Lu, F.-L.; Bruice, T. C. Tetrahedron Lett. 1986, 27, 5967-5970.
43. Wong, W.-H.; Ostovic, D.; Bruice, T. C. J. Am. Chem. Soc. 1987, 109, 3428-3436.
44. Bruice, T. C.; Dicken, C. M.; Balasubramanian, P. N.; Woon, T. C.; Lu, F.-L. J. Am. Chem. Soc. 1987, 109, 3436-3443.
45. Ostovic, D.; Knobler, C. B.; Bruice, T. C. J. Am. Chem. Soc. 1987, 109, 3444-3451.
46. Dicken, C. M.; Balasubramanian, P. N.; Bruice, T. C. Inorg. Chem. 1988, 27, 197-200.
47. Weakley, T. J. R.; Evans, H. T., Jr.; Showell, J. S.; Tourné, G. F.; Tourné, C. M. J. Chem. Soc., Chem. Commun. 1973, 139-140.
48. Finke, R. G.; Droege, M.; Hutchinson, J. R.; Gansow, O. J. Am. Chem. Soc. 1981, 103, 1587-1589.
49. Finke, R. G.; Droege, M.; Domaille, P. J. Inorg. Chem. 1987, 26, 3886-3896.
50. Weakley, T. J. R.; Finke, R. G. Inorg. Chem. 1990, 29, 1235-1241.
51. Gómez-García, C. J.; Casañ-Pastor, N.; Coronado, E.; Baker, L. C. W.; Pourroy, G. J. Appl. Phys. 1990, 67, 5995-5997.
52. Gómez-García, C. J.; Coronado, E.; Borrasalmenar, J. J. Inorg. Chem. 1992, 31, 1667-1673.
53. Casañ-Pastor, N.; Bas-Serra, J.; Coronado, E.; Pourroy, G.; Baker, L. C. W. J. Am. Chem. Soc. 1992, 114, 10380-10383.
54. Gómez-García, C. J.; Borrasalmenar, J. J.; Coronado, E.: Delhaes, P.; Garrigoulagrange, C.; Baker, L. C. W. Synth. Met. 1993, 56, 2023-2027.
55. Gómez-García, C. J.; Coronado, E.; Gómez-Romero, P.; Casañ-Pastor, N. Inorg. Chem. 1993, 32, 3378-3381.
56. Malik, S. A.; Weakley, T. J. R. J. Chem. Soc. A 1968, 2647-2650.
57. Tourné, C. R.; Tourné, G. F.; Malik, S. A.; Weakley, T. J. R. J. Inorg. Nucl. Chem. 1970, 32, 3875-3881.
58. Craig, J. C.; Purushothaman, K. K. J. Org. Chem. 1970, 35, 1721-1722.
59. Powell, M. F.; Pai, E. F.; Bruice, T. C. J. Am. Chem. Soc. 1984, 106, 3277-3285.
60. Connors, K. A. Binding Constants: The Measurement of Molecular Complex Stability; John Wiley & Sons: New York, 1987; Chapter 4.
61. Walker, F. A.; Lo, M.-W.; Ree, M. T. J. Am. Chem. Soc. 1976, 98, 5552-5560.
62. Skoog, D. A. In Principles of Instrumental Analysis, 3rd ed.; Saunders College Publishing: Philadelphia, 1985; Chapter 1.
63. Brown, R. B.; Williamson, M. M.; Hill, C. L. Inorg. Chem. 1987, 26, 1602.
64. Meunier, B. Chem. Rev. 1992, 92, 1411-1456.
65. McMurry, T. J.; Groves, J. T. In Cytochrome P-450; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1986; Chapter 1.
66. Ortiz de Montellano, P. R. In Cytochrome P-450; Ortiz de Montellano, P. R., Ed.; Plenum: New York, 1986; Chapter 7.
67. Ostovic, D.; Bruice, T. C. Acc. Chem. Res. 1992, 25, 314-320.
68. Yang, Y.; Diederich, F.; Valentine, J. S. J. Am. Chem. Soc. 1991, 113, 7195-7205.
69. Mansuy, D. Pure Appl. Chem. 1987, 59, 759-770.
70. Mansuy, D.; Battioni, P. In Activation and Functionalization of Alkanes; Hill, C. L., Ed.; Wiley: New York, 1989; pp 195-218.
71. Katsoulis, D. E.; Pope, M. T. J. Am. Chem. Soc. 1984, 106, 2737-2738.
72. Merbach, A. E. In Inorganic High Pressure Chemistry; van Eldik, R., Ed.; Elsevier: Amsterdam, 1986; p 70.
73. Koola, J. D.; Kochi, J. K. J. Org. Chem. 1987, 52, 4545-4553.
74. Jørgensen, K. A. Chem. Rev. 1989, 89, 431-458.
75. One of the three referees suggested that the complex alkene dependence might be explained by this scenario, namely, a conversion dependent competition between alkene and oxidant derived oxidation products for the reactive intermediate form of the catalyst. We thank the reviewer for this suggestion.