A versatile method for the hydrogen peroxide oxidation of alcohols using PTC condition in tert-butanol

Synlett

Volumn , Issue 5, 2005, Pages 872-874

  Chhikara, Bhupender S ^a   Chandra, Ramesh ^a   Tandon, Vibha ^a  

^a UNIVERSITY OF DELHI   (India)

Author keywords

Alcohols; Hydrogen peroxide; Oxidation; Phase transfer catalyst; Sodium tung state

Indexed keywords

ALCOHOL DERIVATIVE; ALDEHYDE; CARBOXYLIC ACID; HYDROGEN PEROXIDE; KETONE; TERT BUTYL ALCOHOL;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; METHODOLOGY; OXIDATION; PHASE TRANSFER CATALYST; REACTION ANALYSIS;

EID: 15944398320     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-864797     Document Type: Article

References (36)

1. (a) Sheldon, R. A.; Kochi, J. K. Metal-Catalyzed Oxidation of Organic Compounds; Academic Press: London, 1981.
2. (b) Ley, S. V.; Madin, A. In Comprehensive Organic Synthesis, Vol 7; Trost, B. M.; Flemming, I., Eds.; Pergamon: Oxford, 1991, 305-327.
3. (c) Hollingwarth, G. J. In Comprehensive Organic Functional Group Transformations, Vol. 3; Katrizky, A. R.; Meth-Cohn, O.; Rees, C. W.; Pattenden, G., Eds.; Elsevier Science Ltd.: Oxford, 1995, 81-109.
4. (d) Hains, A. H. Methods for the Oxidation of Organic Compounds; Academic Press: New York, 1988.
5. For an overview of alcohol oxidation catalysis, see: (a) Muzart, J. Chem. Rev. 1992, 92, 113.
6. (b) Seddon, K. R.; Stark, A. Green Chem. 2002, 4, 119.
7. (c) Shaabani, A.; Mirzaei, P.; Lee, D. G. Catal. Lett. 2004, 97, 119.
8. (d) Chhikara, B. S.; Chandra, R.; Tandon, V. Tetrahedron Lett. 2004, 45, 7585.
9. (e) Wan, Q. Synlett 2004, 1847.
10. (f) Adak, A. K. Synlett 2004, 1651.
11. (g) Oba, M.; Endo, M.; Nishiyama, K.; Ouchi, A.; Ando, W. Chem. Commun. 2004, 10, 1672.
12. (h) Moorthy, J. N.; Singhal, N.; Venkatakrishnan, P. Tetrahedron Lett. 2004, 45, 5419.
13. (i) Lee, J. C.; Lee, J. Y.; Lee, S. J. Tetrahedron Lett. 2004, 45, 4939.
14. (j) Guo, M.-L. Green Chem. 2004, 6, 271.
15. (k) Reddy, S. R.; Das, S.; Punniyamurthy, T. Tetrahedron Lett. 2004, 45, 3561.
16. (l) Bressette, A. R.; Glover, L. C. I. V. Synlett 2004, 738.
17. (m) Chhikara, B. S.; Tehlan, S.; Kumar, A. Synlett 2005, 63.
18. (n) Pillai, U. R.; Sahle-Demessie, E. Green Chem. 2004, 6, 161.
19. (o) Velusamy, S.; Punniyamurthy, T. Org. Lett. 2004. 6, 217.
20. (p) Tehlan, S.; Hundal, M. S.; Mathur, P. Inorg. Chem. 2004, 43, 6589.
21. (a) Jones, C. W. Application of Hydrogen Peroxide and Derivatives; MPG Books Ltd.: Cornwall UK, 1999.
22. (b) Jorgensen, K. A. Chem. Rev. 1989, 89, 431.
23. (c) Jones, C. W. Application of Hydrogen Peroxide and Derivatives; Royal Society of Chemistry: Cambridge, 1999.
24. (d) Catalytic Oxidations with Hydrogen Peroxide as Oxidant; Strukul, G., Ed.; Kluwer Academic: Dordrecht The Netherlands, 1992.
25. For selected peroxometalate-catalyzed oxidation examples, see: (a) Schultz, H. S.; Freyermuth, H. B.; Buc, S. R. J. Org. Chem. 1963, 28, 1140.
26. (b) Ishi, Y.; Tanaka, H.; Nisiyama, Y. Chem. Lett. 1994, 1.
27. (c) Stec, Z.; Zawadiac, J.; Skibinski, A. C.; Nogueira, H. I. S.; Parkin, B. C. J. Mol. Catal. 1997, 117, 185.
28. (d) Ventrurello, C.; Gambaro, M. J. Org. Chem. 1991, 56, 5924.
29. (e) Arends, I. W. C. E.; Sheldon, R. A.; Wallau, M.; Schuchardt, U. Angew. Chem., Int. Ed. Engl. 1997, 36, 1144.
30. (f) Zennaro, R.; Pinna, F.; Strukul, G.; Arzoumanian, H. J. Mol. Catal. 1991, 70, 269.
31. (a) Noyori, R.; Aoki, M.; Sato, K. Chem. Commun. 2003, 16, 1977.
32. (b) Sato, K.; Takagi, J.; Aoki, M.; Noyori, R. Tetrahedron Lett. 1998, 39, 7549.
33. (c) Sato, K.; Aoki, M.; Takagi, J.; Noyori, R. J. Am. Chem. Soc. 1997, 119, 12386.
34. (d) Sato, K.; Aoki, M.; Takagi, J.; Zimmermann, K.; Noyori, R. Bull. Chem. Soc. Jpn. 1999, 72, 2287.
35. (e) Sato, K.; Hyodo, M.; Takagi, J.; Aoki, M.; Noyori, R. Tetrahedron Lett. 2000, 41, 1439.
36. Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457.