Oxidation of alkenes in supercritical carbon dioxide catalyzed by molybdenum hexacarbonyl

Organometallics

Volumn 17, Issue 20, 1998, Pages 4454-4460

  Haas, Geoffrey R ^a   Kolis, Joseph W ^a  

^a CLEMSON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000594037     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970755n     Document Type: Article

References (58)

1. (a) Sheldon, R. A.; Kochi, J. K Metal Catalyzed Oxidations of Organic Compounds; Academic Press: New York, 1981.
2. (b) Rudolph, J.; Reddy, K. L.; Chiang, J. P.; Sharpless, K. B. J. Am. Chem. Soc. 1997, 119, 6189.
3. (c) Hoft, E. Top. Curr. Chem. 1993, 164, 63.
4. (d) Heaney, H. Aldrichim. Acta 1993, 29, 35.
5. (e) Muzart, J. Chem. Rev. 1992, 92, 113.
6. (f) Jorgenson, K. A. Chem. Rev. 1989, 89, 431
7. (g) Sheldon, R. A.; Kochi, J. K. Adv. Catal. 1976, 25, 343.
8. (h) Tolstikov, G. A.; Yur'ev, U. P.; Dzhemilev, U. M. Russ. Chem. Rev. 1975, 44, 319.
9. (i) Sheldon, R. A. Rec. Trav. Chim. Pays-Bas 1973, 92, 253.
10. (j) Gould, E. S.; Hiatt, R. R.; Irwin, K. C. J. Am. Chem. Soc. 1968, 90, 4573.
11. (k) Hawkins, E. G. E. J. Chem. Soc. 1950, 2, 169.
12. (a) Mimoun, H.; Charpentier, R.; Mitschler, A.; Fischer, J.; Weiss, R. J. Am. Chem. Soc. 1980, 102, 1047.
13. (b) Sheldon, R. A. J. Mol. Catal. 1980, 7, 107.
14. (c) Chong, A. O.; Sharpless, K. B. J. Org. Chem. 1977, 42, 1587.
15. (d) Su, H.; Reed, J. W.; Gould, E. S. Inorg. Chem. 1973, 12, 337.
16. (e) Baker, T. N.; Mains, G. J.; Sheng, M. N.; Zajacek, J. G. J. Org. Chem. 1973, 38, 1145.
17. (f) Sharpless, K. B.; Townsend, J. M.; Williams, D. R. J. Am. Chem. Soc. 1972, 94, 295.
18. (g) Howe, G. R.; Hiatt, R. R. J. Org. Chem. 1971, 36, 2493.
19. (h) Sheldon, R. A.; Kochi, J. K. J. Am. Chem. Soc. 1970, 92, 5175.
20. (a) Landau, R.; Sullivan, G.; Brown, G. A. CHEMTECH 1979, 602.
21. (b) Parshall, G. W. J. Mol. Catal. 1978, 4, 243.
22. (c) Lyons, J. E. Aspects Homogeneous Catal. 1977, 3, 1-136.
23. (d) Brit. Pat. 1249079, 1971, to Shell Oil. U.S. Pat., 3923843, 1975, to Shell Oil.
24. (e) Kollar, J. U.S. Patent 3 360 584, 1967, to Halcon International.
25. (a) Sharpless, K. B.; Kolb, H. C.; VanNieuwenhze, M. S. Chem. Rev. 1994, 94, 2483.
26. (b) Catalytic Asymmetric Synthesis; Ojima, I., Ed.; VCH: New York, 1993, Chapter 4.2, p 160.
27. (c) Schroder, M. Chem. Rev. 1980, 80, 187.
28. (d) Yamada, S.; Mashiko, T.; Terashima, S. J. Am. Chem. Soc. 1971, 99, 1988.
29. (a) Savage, P.; Gopalan, S.; Mizan, T.; Martino, C. J.; Brock, E. E. AIChE J. 1995, 41, 1723.
30. (b) Phelps, C. L.; Smart, N. G.; Wai, C. M. J. Chem. Educ. 1996, 73, 1163.
31. (c) Kaupp, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 1452.
32. (d) Hyatt, J. J. Org. Chem. 1984, 49, 5097.
33. (a) Johnston, J. B.; Hannah, R. E.; Cunningham, V. L.; Daggy, B. P.; Sturm, F. J.; Kelly, R. M. Bio/Technology 1988, 6, 1423.
34. (b) Modell, M.; Larson, J.; Sobezynski, S. F. Tappi J. 1992, 75, 195.
35. (c) Modell, M. In Standard Handbook of Hazardous Waste Treatment and Disposal; Freeman, H. M., Ed.; McGraw-Hill: New York, 1989; Section 8.11.
36. (d) Thomason, T. B.; Hong, G. T.; Swallow, K. C.; Killilea, W. R. In Innovative Hazardous Waste Treatment Technology Series: Thermal Processes; Freeman, H. M., Ed.; Technomic Publishing: Lancaster, PA, 1990; p 31.
37. Korzenski, M. B.; Kolis, J. W. Tetrahedron Lett. 1997, 38, 5611.
38. Holliday, R. L. Dissertation, Clemson University, 1995.
39. Haas, G. R.; Kolis, J. W. Presented at the Southeast, Southwest Regional ACS meeting, Memphis, TN, 1995.
40. (a) Noyori, R. J. Am. Chem. Soc. 1996, 118, 344.
41. (b) Noyori, R.; Jessop, P. G. Tetrahedron Lett. 1996, 37, 2813.
42. (c) Jessop, P. G.; Ikariya, T. K.; Noyori, R. Chem. Rev. 1995, 95, 259.
43. (d) Burk, M. J.; Feng, S.; Gross, M. F.; Tumas, W. J. Am. Chem. Soc. 1995, 117, 8277.
44. (a) Clark, M. J.; Harrison, K. L.; Johnston, K. P.; Howdle, S. M. J. Am. Chem. Soc. 1997, 119, 6399.
45. (b) Kainz, S.; Koch, D.; Baumann, W.; Leitner, W. Angew. Chem., Int. Ed. Engl 1997, 36, 1628.
46. (c) Green Chemistry; Anastas, P. T.; Williamson, T. C., Eds.; ACS Symposium Series 626; American Chemical Society: Washington, DC, 1996; Chapter 11.
47. (d) Monta, D. K.; Tumas, W. Personal communication, 1996.
48. (a) DeSimone, J. M.; Guan, Z.; Elsbernd, C. S. Science 1992, 257, 945.
49. (b) DeSimone, J. M.; Maury, E. E.; Menceloglu, Y. Z.; McClain, J. B.; Romack, T. J.; Combes, J. R. Science 1994, 265, 356.
50. Tanko, J. M.; Blackert, J. F. Science 1994, 263, 203.
51. Haas, G. R.; Schimeck, G. L.; Pennington, W. T.; Kolis, J. W. Acta Crystallogr., in press.
52. Haas, G. R.; Kolis, J. W. Tetrahedron Lett. 1998, 39, 5923.
53. (a) Hirao, T. Chem. Rev. 1997, 97, 2707.
54. (b) Trost, M. K.; Bergman, R. G. Organometallics 1991, 10, 1172.
55. (c) Sheng, M. N.; Zajacek, J. G. J. Org. Chem. 1970, 35, 1839.
56. (d) Sheng, M. N.; Zajacek, J. G. Oxidation of Organic Compounds; 1968; Vol. II, p 418.
57. (e) Brill, W. F.; Indictor, N. J. Org. Chem. 1964, 29, 710.
58. Durbetaki, A. J. Anal. Chem. 1956, 28, 2000.