A versatile cobalt(II)-Schiff base catalyzed oxidation of organic substrates with dioxygen: Scope and mechanism

Tetrahedron

Volumn 53, Issue 22, 1997, Pages 7649-7670

  Punniyamurthy, T ^a   Bhatia, Beena ^a   Reddy, M Madhava ^a   Maikap, Golak C ^a   Iqbal, Javed ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKANONE; EPOXIDE; KETONE;

ARTICLE; CATALYSIS; DRUG PURIFICATION; DRUG SYNTHESIS; ELECTRON SPIN RESONANCE; EPOXIDATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030976836     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00432-8     Document Type: Article

References (58)

1. Sheldon, R. A.; Kochi, J. K. Metal Catalyzed Oxidation of Organic Compounds; Academic Press: New York, 1981; and references cited therein.
2. a) Mimoun, M.; Seree de Roch, I. Tetrahedron, 1975, 31, 777.
3. b) Mimoun, H. J. Org. Chem. 1980, 45, 5387.
4. Murahashi, S. I.; Naota, T.; Hirai, N. ibid, 1993, 58, 7318.
5. a) Irie, R.; Ito, Y.; Katsuki, T. Tetrahedron Lett. 1991, 32, 6891.
6. b) Yamada, T.; Takai, T.; Rhode, O.; Mukaiyama, T. Chem. Lett. 1991, 1.
7. c) Brandes, B. S.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 59, 4378.
8. Backvall, J. E.; Akermark, B.; Ljunggren, S. O. ibid. 1979, 101, 2411.
9. Andrews, M. A.; Kelly, K. P. ibid, 1981, 103, 2894.
10. Tovrog, B. S.; Diamond, S. E.; Szalkiewicz, A. ibid, 1981, 103, 3522.
11. a) Zombek, A.; Hamilton, D. E.; Drago, R. S. ibid, 1982, 104, 6782.
12. (b) Drago, R. S.; Zurich, A.; Nyberg, E. D., ibid, 1985, 107, 1898.
13. Farrer, J.; Holland, D.; Milner, D. J. J. Chem. Soc., Dalton. Trans. 1975, 815.
14. Tezuka, M.; Sekiguchi, O.; Ohkatsu, Y.; Osa. T. Bull. Chem. Soc. Jpn. 1976, 49, 2765.
15. James, B. R.; Kastner, M. Can. J. Chem. 1972, 50, 1698.
16. Peterson, D. H.; Murray, H. C. J. Am. Chem. Soc. 1952, 74, 1871.
17. Hamilton, G. A. ibid 1964, 86, 3391, 8
18. Nishinaga, A.; Tajo, T.; Matsuura, T. J. Chem. Soc., Chem. Comm. 1974, 896.
19. Tabushi, I.; Nakajima, T.; Seto, K. Tetrahedron Lett. 1980, 21, 2565.
20. Petty, R. H.; Welch, B. R.; Wilson, L. J.; Bottomley, L. A.; Kadish, K. M. J. Am. Chem. Soc. 1980, 102, 611.
21. Gunter, M. J.; Mander, L. N.; McLaughlin, G. M.; Murray, K. S.; Berry, K. J.; Clark, P. E.; Buckingham, D. A. ibid 1980, 102, 1470.
22. Munakata, M.; Nishibayashi, S.; Sakamoto, H. J. Chem. Soc., Chem. Comm. 1980, 219.
23. Rawalinson, D. J.; Sosnovsky, G. Synthesis, 1972, 1.
24. Walling, C.; Zavitsas, A, J. Am. Chem. Soc. 1963, 88, 2084.
25. a) Tsuji, J.; Shimizu, I.; Yamamoto, K. Tetrahedron Lett. 1976, 2975.
26. b) Tsuji, J.; Nagashima, H.; Hori, K. Chem. Lett. 1980, 257.
27. a) Groves, J. T. J. Chem. Ed. 1985, 62, 928.
28. b) Groves, J. T.; Quinn, R. J. Am. Chem. Soc. 1985, 107, 5790.
29. Koola, J. D.; Kochi, J. K.; Inorg. Chem. 1987, 26, 908.
30. Jones, R. D.; Summerville, D. A.; Basolo, F. Chem. Rev. 1979, 79, 139.
31. a) Bhatia, B.; Punniyamurthy, T.; Iqbal, J. J. Org. Chem. 1993, 58, 5518.
32. b) Bhatia, S.; Punniyamurthy, T.; Bhatia, B.; Iqbal, J. Tetrahedron, 1993, 49, 6101.
33. c) Punniyamurthy, T.; Bhatia, B.; Iqbal, J. Tetrahedron lett. 1993, 34, 4657.
34. d) Punniyamurthy, T.; Iqbal, J. Tetrahedron Lett. 1994, 35, 2003; 2007.
35. e) Kalra, S. J. S.; Punniyamurthy, T.; Iqbal J.. ibid 1994, 35, 4847.
36. f) Punniyamurthy, T.; Bhatia, B.; Iqbal, J. J. Org. Chem. 1994, 59, 850.
37. g) Reddy, M. M.; Punniyamurthy, T.; Iqbal, J. Tetrahedron Lett. 1995, 36, 159.
38. h) Punniyamurthy, T.; Reddy, M. M.; Kalra, S. J. S.; Iqbal, J. J. Pure Appl. Chem. 1996, 619.
39. Maikap, G. C.; Guhathakurta, D.; Iqbal, J. Syn Lett. 1995, 189.
40. j) Punniyamurthy, T.; Asthana, P.; Kalra, S.J.S.; Iqbal, J. Proc. Indian Acad. Sci. (Chem. Sci.), 1995, 107, 355.
41. k) Iqbal, J.; Bhatia, S.; Reddy, M.M. Synth. Commun. 1993, 23, 2285.
42. 8 that Co(SalMDPT) catalyzes the oxidation of alkenes with dioxygen in ethyl alcohol where the latter acts as a reducing agent during oxygen atom transfer.
43. Busetto, C.; Neri, C.; Palladino, N.; Perrotti, E. Inorg. Chim. Acta. 1971, 5, 129.
44. Nakamoto, K. Infrared and Roman Spectra of Inorganic and Co-ordination Compounds, 4th ed.; Wiley-Interscience: New York, 1986.
45. Cheng, C. K.; Aviles, G.; Bag, N. J. Am. Chem. Soc. 1994, 116, 12127.
46. Harris, D. L.; Loew, G. H. ibid, 1994, 116, 11671.
47. Vos, D. E. D.; Feijen, E. J. P.; Schoonheydt, R. A.; Jacobs, P. A. ibid, 1994, 116, 4746.
48. Marchon, J.-C.; Ramasseul, R. Synthesis, 1989, 389.
49. Mukaiyama, T.; Yamada, T. Bull. Chem. Soc. Jpn. 1995, 68, 17.
50. Yamada, T.; Imagawa, K.; Mukaiyama, T. Chem. Lett. 1992, 2109.
51. Tavares, M.; Ramasseul, R.; Marchon, J.-C.; Bachet, B.; Brassy, C.; Mornon, J.-P. J. Chem. Soc. Perkin Trans. 2, 1992, 1321.
52. Groves, J. T.; Krishnan, S.; Avaria, G. E.; Nemo, T. J. Adv. Chem. Ser. 1980, 191, 277.
53. 2. In analogy with this, it is possible that the carbonyl group will coordinate cis to the bound oxygen in the superoxo complex 1g derived from catalyst 1a.
54. Koola, J. D.; Kochi, J. K. J. Org. Chem. 1987, 52, 4545.
55. Vogel's Textbook of Practical Organic Chemistry, 4th ed.; ELBS; Longman, 1984.
56. Evans, G. J. Chem. Edn. 1959, 241.
57. Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry, 5th ed.; Wiley Interscience; New York, 1988.
58. 32 with the corresponding β-epoxide so in analogy with this the major epoxide from diosgenin acetate and stigmasteryl acetate are assigned α-stereochemistry.