Oxidation of alcohol by lipopathic Cr(VI): A mechanistic study

Journal of Organic Chemistry

Volumn 71, Issue 18, 2006, Pages 6759-6766

  Patel, Sabita ^a   Mishra, B K ^a  

^a SAMBALPUR UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; CHROMIUM COMPOUNDS; DATA ACQUISITION; ENTROPY; ESTERS; OXIDATION; REACTION KINETICS; SURFACE ACTIVE AGENTS;

CETYLTRIMETHYLAMMONIUM DICHROMATE (CTADC); DICHLOROMETHANE (DCM); MICELLAR SYSTEM; MICHAELIS-MENTEN TYPE KINETICS;

ALCOHOLS;

ACID; ALCOHOL; CATIONIC SURFACTANT; CETYLTRIMETHYLAMMONIUM DICHROMATE; CHROMIUM; DICHLOROMETHANE; SURFACTANT; TRIMETHYLAMMONIUM SALT DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; ENTROPY; EQUILIBRIUM CONSTANT; MICHAELIS MENTEN KINETICS; OXIDATION; TEMPERATURE;

ALCOHOLS; CETRIMONIUM COMPOUNDS; CHROMIUM; ELECTROSTATICS; HYDROPHOBICITY; KINETICS; MECHANICS; METHYLENE CHLORIDE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; SOLVENTS;

EID: 33750438435     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0608772     Document Type: Article

References (54)

1. (a) Corey, E. J.; Suggs, W. J. Tetrahedron Lett. 1975, 2647.
2. (b) Corey, E. J.; Schmidt, G. Tetrahedron Lett. 1979, 399.
3. (c) Antonioletti, R.; D'Auria, M.; Piancatelle, G.; Scettri, A. Tetrahedron Lett. 1981, 1041.
4. (d) Still, W. C.; Galynker, I. J. Am. Chem. Soc. 1982, 104, 1774.
5. (e) D'Auria, M.; Mico, A. D.; D'Onofrio, F.; Scettri, A. Synthesis 1985, 988.
6. (f) Cossio, F. P.; Aizpurua, J. M.; Palomo, C. Can. J. Chem. 1986, 64, 225.
7. (g) Banerji, K. K. J. Chem. Soc., Perkin Trans. 2 1988, 2065.
8. (h) Corey, E. J.; Boger, D. L. Tetrahedron Lett. 1978, 2461.
9. (i) Yli-Kauhaluoma, J. T.; Harwig, C. W.; Wentworth, P., Jr.; Janda, K. D. Tetrahedron Lett. 1998, 39, 2269.
10. (j) Maki, S.; Ishihara, J.; Nakanishi, K. J. Indian Chem. Soc. 2000, 77, 651.
11. (k) Alcudia, A.; Arrayas, R. G.; Liebeskind, L. S. J. Org. Chem. 2002, 67, 5773.
12. (l) Tajbakhsh, M.; Hosseinzadeh, R.; Shakoori, A. Tetrahedron Lett. 2004, 45, 2647.
13. (a) Dey, D.; Mahanti, M. K. J. Org. Chem. 1990, 55, 5848.
14. (b) Chaubey, G. S.; Das, S.; Mahanti, M. K. Can. J. Chem. 2003, 81, 204.
15. (c) Kuotsu, B.; Tiewsoh, E.; Debroy, A.; Mahanti, M. K. J. Org. Chem. 1996, 61, 8875.
16. Shirini, F.; Mohammadpoor-Baltrok, I.; Hejazi, Z.; Heravi, P. Bull. Korean Chem. Soc. 2003, 24, 517.
17. Agarwal, S.; Tiwari, H. P.; Sharma, J. P. Tetrahedron 1990, 46, 1963.
18. (a) Cossio, F. P.; Lopez, M. C.; Palomo, C. Tetrahedron 1987, 43, 3963.
19. (b) Sekar, K. G. J. Chem. Res. 2002, 2002, 626.
20. Patel, S.; Mishra, B. K. J. Org. Chem. 2006, 71, 3522.
21. (a) Okimoto, T.; Swern, D. J. Am. Oil Chem. Soc. 1977, 54, 862A.
22. (b) Sala, T.; Sargent, M. V. J. Chem. Soc., Chem. Commun. 1978, 253.
23. (c) Schmidt, H. J.; Schafer, H. J. Angew. Chem., Int. Ed. Engl. 1979, 18, 78.
24. (d) Lee, D. G.; Brown, K. C. J. Am. Chem. Soc. 1982, 104, 5076.
25. (e) Karaman, H.; Barton, R. J.; Robertson, B. E.; Lee, D. G. J. Org. Chem. 1984, 49, 4509.
26. (a) Lee, D. G.; Brown, K. C.; Karaman, H. Can. J. Chem. 1986, 64, 1054.
27. (b) Shukla, R.; Kothari, S.; Kotai, L.; Banerji, K. K. J. Chem. Res. 2001, 127.
28. (c) Shukla, R.; Sharma, P. K.; Kotai, L.; Banerji, K. K. Proc. Indian Acad. Sci. (Chem. Sci.) 2003, 115, 129.
29. Dash, S.; Mishra, B. K. Indian J. Chem. 1997, 36A, 662.
30. Dash, S.; Mishra, B. K. Int. J. Chem. Kinet. 1995, 27, 627.
31. Bora, U.; Chaudhuri, M. K.; Day, D.; Kalita, D.; Kharmawphlang, W.; Mandal, G. C. Tetrahedron 2001, 57, 2445.
32. (a) Patel, S.; Mishra, B. K. Tetrahedron Lett. 2004, 45, 1371.
33. (b) Patel, S.; Kuanar, M.; Nayak, B. B.; Banichul, H.; Mishra, B. K. Synth. Commun. 2005, 35, 1033.
34. (c) Sahu, S.; Patel, S.; Mishra, B. K. Synth. Commun. 2005, 35, 3123.
35. Saraswat, S.; Sharma, V.; Banerji, K. K. Proc. Indian. Acad. Sci. (Chem. Sci.) 2003, 115, 75.
36. Cotton, F. A.; Wilkinson, G.; Murillo, C. A.; Bochmann, M. In Advanced Inorganic Chemistry, 6th ed.; John Wiley & Sons: New York, 1999; p 747.
37. Kuotsu, B.; Tiewsoh, E.; Debroy, A.; Mahanti, M. K. J. Org. Chem. 1996, 61, 8875.
38. Banerji, K. K. Bull. Chem. Soc. Jpn. 1978, 51, 2732.
39. Rocek, J.; Westheimer, F. J.; Eschenmoser, A.; Moldovanyi, L.; Schreiber, J. Helv. Chim. Acta 1962, 45, 2554.
40. Lee, D. G.; Stewart, R. J. Org. Chem. 1967, 32, 2868.
41. Rosso, F. D.; Bartoletti, A.; Profio, D. P.; Germani, R.; Savelli, G.; Blasko, A.; Bunton, C. A. J. Chem. Soc., Perkin Trans. 2 1995, 673.
42. Davies, J. T. Proc. Int. Congr. Surf. Act. 2nd 1957, 1, 426.
43. Leo, A.; Hansch, C.; Elkins, D. Chem. Rev. 1971, 71, 525.
44. Randic, M. J. Am. Chem. Soc. 1975, 97, 6609.
45. (a) Gladilin, A. K.; Levashov, A. V. Biochemistry (Moscow) 1998, 63, 408.
46. (b) Maurel, P. J. Biol. Chem. 1978, 253, 1677.
47. Taft, R. W.; Abboud, J. L. M.; Kamlet, M. J. J. Org. Chem. 1984, 49, 2001.
48. Katritzky, A. R.; Para, D. C.; Kuanar, M.; Hur, E.; Karelson, M. J. Phys. Chem. A 2005, 109, 10323.
49. Swain, C. G.; Swain, M. S.; Powel, A. L.; Alunni, S. J. Am. Chem. Soc. 1983, 105, 502.
50. Brandstrom, A. Adv. Phys. Org. Chem. 1977, 15, 267.
51. Starks, C. M.; Owens, R. M. J. Am. Chem. Soc. 1973, 95, 3616.
52. Kumbhat, V.; Sharma, P. K.; Banerji, K. K. Indian J. Chem. 2000, 39A, 1169.
53. Vogel, A. I. In A Textbook of Quantitative Inorganic Analysis, 3rd ed.; ELBS and Longmans: U.K., 1961.
54. Riddick, J. A.; Hunger, W. B. Organic Solvents; Techniques of Chemistry, Vol. II, Wiley-Interscience: New York, 1970.