A simple biomimetic protocol for the oxidation of alcohols with sodium hypochlorite in the presence of β-cyclodextrin in water

Canadian Journal of Chemistry

Volumn 82, Issue 7, 2004, Pages 1230-1233

  Surendra, K ^a   Krishnaveni, N Srilakshmi ^a   Rao, K Rama ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

cyclodextrin; Alcohols; Biomimetic; KBr; Oxidation; Sodium hypochlorite; Water

Indexed keywords

BIOMIMETIC MATERIALS; OXIDATION; SODIUM COMPOUNDS; SOLVENTS;

CARBONYL COMPOUNDS; ROOM TEMPERATURE; SODIUM HYPOCHLORITE;

ALCOHOLS;

ALCOHOL; BETA CYCLODEXTRIN; HYPOCHLORITE SODIUM; WATER;

ARTICLE; BIOMIMETICS; CHEMICAL ANALYSIS; OXIDATION; REACTION ANALYSIS; ROOM TEMPERATURE;

EID: 10644263221     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v04-065     Document Type: Article

References (53)

1. (a) P.T. Anastas and J.C. Warner. In Green chemistry, theory and practice. Oxford University Press, Oxford. 1998;
2. (b) P.T. Anastas and T.C. Williamson (Editors). Green chemistry, frontiers in benign chemical synthesis and processes. Oxford University Press, Oxford. 1998;
3. (c) P.T. Anastas, L.G. Heine, and T.C. Williamson (Editors). Green engineering. ACS Symposium Series. Vol. 766. American Chemical Society, Washington, D.C. 2000;
4. (d) J. Clark and D. Macquarrie (Editors). Handbook of green chemistry & technology. Blackwell, Oxford. 2002;
5. (e) M. Eissen, J. O. Metzger, E. Schmidt, and U. Schneidewind. Angew. Chem. Int. Ed. 41, 414 (2002).
6. (a) R.A. Sheldon, I.W.C.E. Arends, and A. Dijksman. Catal. Today, 57, 157 (2000);
7. (b) T. Mallat and A. Baiker. Catal. Today, 19, 247 (1994).
8. M. Hudlicky. Oxidations in organic chemistry. American Chemical Society Monograph 186. American Chemical Society, Washington, D.C. 1990.
9. (a) J.D. Albright and L. Goldman. J. Am. Chem. Soc. 87, 4214 (1965);
10. (b) K.E. Pitzner and J.G. Moffatt. J. Am. Chem. Soc. 87, 5661 (1965);
11. (c) K.E. Pitzner and J.G. Moffatt. J. Am. Chem. Soc. 87, 5670 (1965);
12. (d) R.J. Parikh and W.E. Doering. J. Am. Chem. Soc. 89, 5505 (1967);
13. (e) W.W. Epstein and F.W. Sweat. Chem. Rev. 67, 247 (1967);
14. (f) K. Omura, A.K. Sharma, and D. Swern. J. Org. Chem. 41, 957 (1976).
15. (a) G. Cainelli and G. Cardillo. Chromium oxidations i organic chemistry. Springer, New York. 1984;
16. (b) S.V. Ley and A. Madin. In Comprehensive organic synthesis. Edited by B.M. Trost and I. Fleming. Pergamon Press, Oxford. 1991. pp. 7, 251;
17. (c) E.J. Corey and G. Schmidt. Tetrahedron Lett. 399 (1979).
18. (a) R.A. Sheldon, I.W.C.E. Arends, and A. Dijksman. Catal. Today, 57, 157 (2000);
19. (b) M. Hayashi and H.J. Kawabata. Synth. Org. Chem. Jpn. 60, 137 (2002);
20. (c) M. Hayashi and H.J. Kawabata. Synth. Org. Chem. Jpn. 60, 1625 (2002);
21. (d) S.V. Ley, W.P. Griffith, and S.P. Marsden. Synthesis, 639 (1994).
22. M.R. Leanna, T.J. Sowin, and H.E. Morton. Tetrahedron Lett. 33, 5029 (1992).
23. V.M. Dembitsky. Tetrahedron, 59, 4701 (2003).
24. (a) K. Omura and D. Swern. Tetrahedron, 34, 1651 (1978);
25. (b) A.J. Mancuso and D. Swern. Synthesis, 165 (1981).
26. (a) D.B. Dess and J.C. Martin. J. Org. Chem. 48, 4155 (1983);
27. (b) D.B. Dess and J.C. Martin. J. Am. Chem. Soc. 113, 7277 (1991);
28. (c) J.B. Plumb and D.J. Harper. Chem. Eng. News, 68(29), 3 (1990).
29. P.H.J. Carlsen, T. Katsuki, V.S. Martin, and K.B. Sharpless. J. Org. Chem. 46, 3936 (1981).
30. R.G. Vaghei and A. Khazaei. Tetrahedron Lett. 44, 7525 (2003).
31. (a) A.J. Fatiadi. Synthesis, 133 (1976);
32. (b) L.A. Paquette (Editor). Encyclopedia of reagents for organic synthesis. Wiley, Chichester. 1995.
33. (a) J-i. Matsuo, D. Iida, H. Yamnaka, and T. Mukaiyama. Tetrahedron, 59, 6739 (2003);
34. (b) T. Mukaiyama, J-i. Matsuo, D. Iida, and H. Kitagawa. Chem. Lett. 846 (2001).
35. (a) R. Filler. Chem. Rev. 63, 21 (1963);
36. (b) J. Einhorn, C. Einhorn, F. Ratajczak, and J.L. Pierre. J. Org. Chem. 61, 7452 (1996).
37. (a) J. Yoshida, R. Nakai, and N. Kawabata. J. Org. Chem. 45, 5269 (1980);
38. (b) C.R. Harrison and P. Hodge. J. Chem. Soc., Perkin Trans, 1, 509 (1982).
39. T. Mallat and A. Baiker. Catal. Today, 19, 247 (1994).
40. (a) G.A. Lee and H.H. Freedman. Tetrahedron Lett. 1641 (1976);
41. (b) S.L. Regen. J. Org. Chem. 42, 875 (1997).
42. R.V. Stevens, K.T. Chapman, and H.N. Weller. J. Org. Chem. 45, 2030 (1980).
43. P.L. Anelli, C. Biffi, F. Montanari, and S. Quici. J. Org. Chem. 52, 2559 (1987).
44. (a) K. Surendra, N.S. Krishnaveni, Y.V.D. Nageswar, and K.R. Rao. J. Org. Chem. 68, 4994 (2003);
45. (b) K. Surendra, N.S. Krishnaveni, M.A. Reddy, Y.V.D. Nageswar, and K.R. Rao. J. Org. Chem. 68, 2058 (2003);
46. (c) N.S. Krishnaveni, K. Surendra, M.A. Reddy, Y.V.D. Nageswar, and K.R. Rao. J. Org. Chem. 68, 2018 (2003);
47. (d) N.S. Krishnaveni, K. Surendra, Y.V.D. Nageswar, and K.R. Rao. Synthesis, 1968 (2003).
48. R. Breslow. Acc. Chem. Rec. 13, 170 (1980).
49. S. Banfi and S. Colonna. Synth. Commun. 1049 (1983).
50. K.R. Rao and P.B. Sattur. J. Chem. Soc. Chem. Commun. 342 (1989).
51. J. Szejtli and T. Osa. In Comprehensive supramolecular chemistry. Vol. 3. Pergamon Press, Oxford, UK. 1996. p. 253.
52. P.V. Demarco and A.L. Thakkar. J. Chem. Soc. Chem. Commun. 2 (1970).
53. 1H FT-NMR spectra. Aldrich, Milwaukee, Wis. 1985-1989.