Kinetics of selective formation of ibuprofenamide by phase transfer catalyzed oxidation of 2-(4-isobutylphenyl)propionitrile with basic hydrogen peroxide

Organic Process Research and Development

Volumn 12, Issue 4, 2008, Pages 740-747

  Yadav, Ganapati D ^a   Ceasar, J Leo ^a  

^a INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

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EID: 58149235224     PISSN: 10836160     EISSN: 1520586X     Source Type: Journal    
DOI: 10.1021/op7002425     Document Type: Article

References (55)

1. Stark, C. M.; Liotta, C.; Halpern, M. Phase Transfer Catalysis: Fundamentals, Application, and Industrial perspectives; Chapman and Hall Publication: New York, 1994.
2. Sasson, Y., Neumann, R., Eds. Handbook of Phase Transfer Catalysis; Blackie Academic and Professional: London, 1997.
3. Dehmlow, E. V.; Dehmlow, S. S. Phase Transfer Catalysis, 3rd ed.; VCH: New York, 1993.
4. Weber, W. P.; Gokel, G. W. Phase Transfer Catalysis in Organic Synthesis; Springer-Verlag: Berlin, 1977.
5. Halpern, M. E. Phase Transfer Catalysis: Mechanisms and Syntheses; American Chemical Society: Washington, DC, 1997.
6. Yadav, G. D. Chem. Ind. Digest 2004, 17, 52.
7. Yadav, G. D. Top. Catal 2004, 29, 143-158.
8. Yadav, G. D. Chim. Ind. 2000, 1.
9. Furniss, B. S., Hannaford, A. J. , Smith, P. W. G., Tatchell A. R., Eds. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Longman: London, 1989.
10. (a) Dopp, D., Dopp, H., Eds. Methoden der Organischen Chemie (Houben-Weyl); Thieme: Stuttgart, 1985; Vol. E5, 2, p 1024.
11. (b) Brown, B. R., Ed.; The Organic Chemistry of Aliphatic Nitrogen Compounds; Oxford University Press: Oxford, 1994; pp217-342.
12. March, J. Advanced Organic Chemistry, 3rd. ed.; Wiley-Interscience: New York, 1985; p 788.
13. Doshi, A.; Samant, S. D.; Deshpande, S. G. Indian J. Pharm. Sci. 2002, 64, 440-444.
14. Rajasekaran, A.; Sivakumar, P.; Jayakar, B. Indian J. Pharm. Sci. 1999, 61, 158-161.
15. Schaefer, F. C. In The Chemistry of the Cyano Group; Rappaport, Z., Ed.; Interscience: New York, 1970; p 239.
16. Bauer, W., Jr. In Ullmann's Encyclopedia of Industrial Chemistry, 5th ed.; Wiley: New York, 1990; Vol. A16, p 441.
17. Mckenzie, B. F.; Kendall, E. C. In Organic Syntheses; Gilman, H., Blatt, A. H., Eds.; Wiley: New York, 1941; Collect. Vol. 1, p 21.
18. (a) Li, L.; Lin, K. H.; Hung, Y. T.; Kang, S. A. J. Chin. Chem. Soc. 1942, 9, 1, 14; 31;
19. Chem. Abstr. 1944, 335.
20. (b) Westfahl, J. C.; Gresham, T. L. J. Am. Chem. Soc. 1955, 77, 3961.
21. (a) Hall, J.; Gisler, M. J. Org. Chem. 1976, 41, 3769.
22. (b) Linke, S. Synthesis 1978, 303.
23. Edward, J. T.; Meacock, S. C. R. J. Chem. Soc. 1957, 2000.
24. Matsuda, F. Chem, Technol. 1977, 7, 306.
25. Ravindranathan, M.; Kalyanam, N.; Sivaram, S. J. Org. Chem. 1982, 47, 4812.
26. Zil'berman, E. N. Russ. Chem. Rev. Engl. Transl. 1984, 53, 900.
27. Izumi, Y. Catal. Today 1997, 33, 371.
28. Brown, B. R. The Organic Chemistry of Aliphatic Nitrogen Compounds; Oxford University Press: New York, 1994; pp 175-259.
29. Jensen, C. M.; Trogler, W. C. J. Am. Chem. Soc. 1986, 108, 723.
30. Kaminskaia, M. V.; Kostic, N. M. J. Chem. Soc., Dalton Trans. 1996, 3677.
31. Ghaffar, T.; Parkins, A. W. Tetrahedron 1995, 40, 8657.
32. Watanabe, K. Bull. Chem. Soc. Jpn. 1959, 32, 1280.
33. Watanabe, K. Bull. Chem. Soc. Jpn. 1964, 37, 1325.
34. Watanabe, K. Bull. Chem. Soc. Jpn. 1967, 40, 1660.
35. Watanabe, K. Bull. Chem. Soc. Jpn. 1971, 44, 1440.
36. Bernard, B. J. Chem. Soc. (A) 1969, 2140.
37. Katrizky, A. R.; Pilarski, B.; Urogei, L. Synthesis 1989, 949.
38. Krewson, C. F.; Couch, J. F. J. Am. Chem. Soc. 1943, 65, 2256.
39. (a) Noller, C. R. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. 2, p 586.
40. (b) Buck, J. S. Organic Syntheses; Wiley: New York, 1943; Collect. Vol. 2, p 44.
41. (c) Wiberg, K. B. J. Am. Chem. Soc. 1953, 75, 3961.
42. (d) Mcisaac, J. E., Jr.; Ball, R. E.; Behrman, E. J. J. Org. Chem. 1971, 36, 3048.
43. (a) Hendrickson, J. B.; Blair, K. W.; Keehn, P. M. Tetrahedron Lett. 1976, 17, 603.
44. (b) Cacei, C.; Misiti, D.; La Torre, F. Synthesis 1980, 243.
45. Spickett, R. G. W.; Vega, A.; Prieto, J.; Moragues, J.; Marquez, M.; Roberts, D. J. Eur. J. Med. Chem. - Chim, Ther. 1976, 11, 7.
46. (a) WO 2000 0024 710, 2000.
47. (b) WO 2002 062 330, 2002.
48. (c) U.S. Patent 2004 102 520, 2004.
49. (a) Snell, D.; Colby, J. Enzyme Micro. Technol. 1999, 24, 160.
50. (b) Bornscheuer, U. T.; Kazluaskas, R. J. Hydrolases in Organic Synthesis, 2nd ed.; Wiley-ECH: New York, 2006.
51. (c) Roberts, S. M.,. Ed. Biocatalysis for Organic Synthesis; Wiley: New York, 1999.
52. (d) Yadav, G. D.; SajgureA. D.;.; Dhoot, S. B. Enzyme Catalysis in Fine Chemical and Pharmaceutical Industries. In Enzyme Mixtures and Complex Biosynthesis; Bhattacharya, S. K., Ed.; Landes Bioscience: New York, 2007; Chapter 8, pp 79-106.
53. Wiberg, K. B. J. Am. Chem. Soc 1953, 75, 3961.
54. Yadav, G. D.; Jadhav, Y. B. Langmuir 2002, 18, 5995.
55. Yadav, G. D.; Jadhav, Y. B. J. Mol. Cat. A: Chem. 2002, 184, 151.