Mechanism of the Chromium-Catalyzed Epoxidation of Olefins. Role of Oxochromium(V) Cations

Journal of the American Chemical Society

Volumn 107, Issue 25, 1985, Pages 7606-7617

  Samsel, E G ^a   Srinivasan, K ^a   Kochi, J K ^a  

^a UNIVERSITY OF HOUSTON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 3042863400     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00311a064     Document Type: Article

References (24)

1. For a review, see: Sheldon, R. A.; Kochi, J. K. “Metal-Catalyzed Oxidations of Organic Compounds”; Academic: New York 1981.
2. See: Berti, G. “Topics in Stereochemistry”; Allinger, N. L., Eliel, E. L. Eds.; Wiley: New York, 1973; Vol. V. Rappe', A. K.; Goddard, W. A., III J. Am. Chem. Soc. 1982, 104, 3287.
3. Groves, J. T.; McClusky, G. A. J. Am. Chem. Soc. 1976, 98, 859. (b) Groves, J. T.; Nemo, T. E.; Myers, R. S. J. Am. Chem. Soc. 1979, 101, 1032. (c) See also: Guengerich, F. P.; McDonald, T. L. Acc. Chem. Res. 1984, 17, 9.
4. Groves, J. T.; Kruper, W. J., Jr. J. Am. Chem. Soc. 1979, 101, 7613. (b) Groves, J. T.; Myers, R. S. J. Am. Chem. Soc. 1983, 105, 5791. (c) Smegal, J. A.; Hill, C. L. J. Am. Chem. Soc. 1983, 105, 3515. (d) Yuan, L. C.; Bruice, T. C. J. Am. Chem. Soc. 1985, 107, 512, for leading references.
5. Siddall, T. L.; Miyaura, N.; Kochi, J. K. J. Chem. Soc., Chem. Commun. 1983, 1185.
6. Srinivasan, K.; Kochi, J. K. Inorg. Chem., in press.
7. 1 species is 1.73 μB(b) Determined by the Evans method. Evans, D. F. J. Chem. Soc. 1959, 2003. See also: Jolly, W. L. “The Synthesis and Characterization of Inorganic Compounds”; Prentice-Hall: Englewood Cliffs, NJ, 1971; pp 375–378.
8. Isotropic (g) values in the range 1.978-1.988 have been reported for a variety of chromium(V) species. See: Kon, J. H. J. Inorg. Nucl. Chem. 1963, 25, 933. Krumpolc, M.; DeBoer, B. G.; Rocek, J. J. Am. Chem. Soc. 1978, 100, 145. Freeman, F.; Armstead, C. R.; Essig, M. G.; Karchefski, E. M.; Kojima, C.; Manopolie, V. C.; Wickman, A. H. J. Chem. Soc., Chem. Commun. 1980, 65. Wiberg, K. B.; Schaefer, H. J. Am. Chem. Soc. 1969, 91, 933. Garifyanov, N. S.; Kozyrev, B. M.; Fedofov, V. N. Dokl. Akad. Nauk. SSSR 1968, 178, 808.
9. For a review, see: Mitewa, M.; Bontchev, P. R. Coord. Chem. Rev. 1985, 61, 281. See also: Griffith, W. P. Coord. Chem. Rev. 1970, 5, 459.
10. 33 could also lie as methylene complexes with chromium. Cf.: Fischer, E. O., Adv. Organomet. Chem. 1976, 14, 1.
11. Basolo, F.; Pearson, R. G. “Mechanisms of Inorganic Reactions”, 2nd ed.; Wiley: New York, 1967; p 124ff.
12. Coggon, P.; McPhail, A. T.; Mabbs, F. E.; Richards, A.; Thornley, A. S. J. Chem. Soc. A 1970, 3296.
13. Nelson, J. H.; Garvey, R. G.; Ragsdale, R. O. Coord. Chem. Rev. 1968, 3, 375; J. Heterocyclic Chem. 1967, 4, 951.
14. For a recent discussion of the mechanistic problem of delineating the transition state of oxygen atom transfer, see; Miyaura. N.; Kochi, J. K. J. Am. Chem. Soc. 983, 105, 2368.
15. Sharpless, K. B.; Teranishi, A. Y.; Backvall, J. E. J. Am. Chem. Soc. 1977, 99, 3120.
16. Rice, F. O.; Teller, E. J. Chem. Phys. 1938, 6, 489. (b) Hine, J. Adv. Phys. Org. Chem. 1977, 15, 1.
17. Broos, R.; Anteunis, M. Synth. Commun. 1976, 6, 53.
18. Perrin, D. D.; Armarego, W. L.; Perrin, D. R. “Purification of Laboratory Chemicals”; Pergamn: New York, 1980.
19. Swern, D. Org. React. 1953, 7, 378.
20. Pfeiffer, P.; Breith, E.; Lubbe, E.; Tsumaki, T. Liebigs Ann. 1933, 503, 84.
21. Sayre, R. J. Am. Chem. Soc. 1955, 77, 6690.
22. Saltzman, H.; Sharefkin, J. G. “Organic Syntheses”; Wiley: New York, 1973; Collect. Vol. 5, p 658.
23. Ochiai, E. J. Org. Chem. 1953, 18, 534.
24. Staudinger, H.; Hauzer, E. Helv. Chim. Acta 1921, 4, 861.