Studies on oxidations with IBX: Oxidation of alcohols and aldehydes under solvent-free conditions

Tetrahedron Letters

Volumn 45, Issue 28, 2004, Pages 5419-5424

  Moorthy, Jarugu Narasimha ^a   Singhal, Nidhi ^a   Venkatakrishnan, P ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

Alcohols; IBX; Oxidations; Solvent free

Indexed keywords

ALCOHOL; ALDEHYDE; BENZOIC ACID DERIVATIVE; SOLVENT;

ALCOHOL OXIDATION; ARTICLE; CHEMICAL REACTION; DESS MARTIN OXIDATION; HEAT TREATMENT; HIGH TEMPERATURE; OXIDATION KINETICS; PHASE TRANSITION; REACTION ANALYSIS;

EID: 2942643906     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.044     Document Type: Article

References (29)

1. Noyori R., Aoki M. Chem. Commun. 2003;1977-1986
2. Brink G.-J.T., Arends I.W.C.E., Sheldon R.A. Science. 287:2000;1636-1639
3. Nicolaou K.C., Baran P.S. Angew. Chem. Int. Ed. 41:2002;2678-2720
4. Zhdankin V.V., Stang P.J. Chem. Rev. 102:2002;2523-2584
5. Wirth T. Angew. Chem. Int. Ed. 40:2001;2812-2814
6. Hartmann C., Meyer V. Chem. Ber. 26:1893;1727
7. Frigerio M., Santagostino M. Tetrahedron Lett. 43:1994;8019-8022
8. Frigerio M., Santagostino M., Sputore S., Palmisano G. J. Org. Chem. 60:1995;7272-7276
9. Nicolaou K.C., Mathison C.J.N., Montagnon T. Angew. Chem. Int. Ed. 42:2003;4077-4082
10. Nicolaou K.C., Mathison C.J.N., Montagnon T. J. Am. Chem. Soc. 126:2004;5192-5201
11. Shukla V.G., Salgaonkar P.D., Akamanchi K.G. J. Org. Chem. 68:2003;5422-5425
12. Magdziak D., Rodriguez A.A., Water R.W.V.D., Pettus T.R.R. Org. Lett. 4:2002;285-288
13. Wu Y., Huang J.-H., Shen X., Hu Q., Tang C.-J., Li L. Org. Lett. 4:2002;2141-2144
14. Surendra K., Krishnaveni N.S., Reddy M.A., Nageswar Y.V.D., Rao K.R. J. Org. Chem. 68:2003;9119-9121
15. Ozzane A., Pouysegu L., Depernet D., Francois B., Quideau S. Org. Lett. 5:2003;2903-2906
16. Thottumkara A.P., Vinod T.K. Tetrahedron Lett. 43:2002;569-572
17. Zhdankin V.V., Smart J.T., Zhao P., Kiprof P. Tetrahedron Lett. 41:2000;5299-5302
18. Zhdankin V.V., Koposov A.Y., Netzel B.C., Yashin N.V., Rempel B.P., Freguson M.J., Tykwinski R.R. Angew. Chem. Int. Ed. 42:2003;2194-2196
19. Mulbaier M., Giannis A. Angew. Chem. Int. Ed. 40:2001;4393-4394
20. Liu Z., Chen Z.-C., Zheng Q.-G. Org. Lett. 5:2003;3321-3323
21. Surendra K., Krishnaveni N.S., Reddy M.A., Nageswar Y.V.D., Rao K.R. J. Org. Chem. 68:2003;2058-2059
22. More J.D., Finney N.S. Org. Lett. 4:2002;3001-3003
23. Moorthy J.N., Singhal N., Mal P. Tetrahedron Lett. 45:2004;309-312
24. The typical experimental procedure involved heating the mixture of alcohol/aldehyde and finely powdered IBX in a Kugelrohr (glass oven, Buchi) at 60-70°C (for alcohols) or at 90°C (for aldehydes) for the appropriate durations given in Tables 1-3. For liquid substrates, their ether solutions were treated with finely powdered IBX, the solvent removed and the solid admixture thus formed was heated. In the case of crystalline substrates, IBX and the substrate were ground together with a mortar and pestle, and the admixture was heated in a Kugelrohr oven. Filtration of the reaction mixture over a short-pad of silica gel afforded the aldehydes/acids. The IBX employed for the reactions was prepared by the reported procedure, see: Boeckman, R. K., Jr.; Shao, P.; Mullins, J. J. Org. Synth. 77, 141
25. The exclusion of water may occur either by homolysis involving a single electron transfer mechanism (SET) or by heterolysis. The former has been proposed in the case of oxidation of electron-rich amines, see: Ref. [5b]. A similar SET process is unlikely in the case of alcohols
26. Nicolaou K.C., Zhong Y.-L., Baran P.S. J. Am. Chem. Soc. 122:2000;7596-7597
27. Mazitschek R., Mulbaier M., Giannis A. Angew. Chem. Int. Ed. 41:2002;4059-4061
28. Frigerio M., Santagostino M., Sputore S. J. Org. Chem. 64:1999;4537-4538
29. Plumb, J. B.; Harper, D. J. Chem. Eng. News 1990, July 16, 3