Role of Hexafluoro-2-propanol in Selective Oxidation of Sulfide to Sulfoxide: Efficient Preparation of Glycosyl Sulfoxides

European Journal of Organic Chemistry

Volumn , Issue 12, 1998, Pages 2937-2940

  Ravikumar, K S ^a   Zhang, Yong Min ^b   Bégué, Jean Pierre ^a   Bonnet Delpon, Danièle ^a  

^a UNIVERSITÉ PARIS SUD   (France)

^b ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

Fluorine; Glycosides; Hydrogen bonds; Oxidation; Peroxides

Indexed keywords

EID: 0001692962     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(199812)1998:12<2937::aid-ejoc2937>3.0.co;2-d     Document Type: Article

References (33)

1. [1a] E. Block, J. Chem. Educ. 1971, 48, 814-824.
2. [1b] I. Fleming, Chem. Ind. (London) 1975, 449.
3. [1c] E. Block, Reactions of Organosulfur Compounds, Academic Press, New York, 1978.
4. [1d] T. Durst, Comprehensive Organic Chemistry (Eds.: D. H. R. Barton, W. D. Ollis), vol. 3, Pergamon, Oxford, 1979.
5. D. Kahne, S. Walker, Y. Cheng, D. Van Engen, J. Am. Chem. Soc., 1989, 111, 6881-6882.
6. J. Drabowicz, P. Kielbasinski, M. Mikolajczyk, The Chemistry of Sulfones and Sulfoxides, (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling), Wiley, New York, 1988, p. 233.
7. Oxidations in Organic Chemistry (Ed: M. Hudlicky), ACS Monograph 186, American Chemical Society, Washington, D C., 1990. p. 252.
8. D. Barnard, L. Bateman, J I. Cunneen. Organic Sulfur Compounds, vol. 1 (Ed.: N. Kharasch), Pergamon Press, New York, 1961, p. 229-247.
9. C. R. Johnson, J. E. Keiser, Org. Synth. Coll. Vol. V 1973, 791-793.
10. [7a] C. G. Overberger, R. W. Cummins, J. Am Chem. Soc. 1953, 5, 4783-4787.
11. [7b] J. Drabowiez, P. Lyzwa, M. Popielarczyk, M. Mikolajczyk, Synthesis, 1990, 937-938.
12. [8a] D Ramkumar, S. Sankararaman, Synthesis 1993, 1057-1058,
13. [8b] R. Y. Yang, L. X. Dai, Synth. Commun. 1994, 24, 2229-2236.
14. [8c] M. Hirano, S. Yakabe, S. Itoh, J. H. Clark, T. Morimotoa, Synthesis 1997, 1161 and references cited.
15. [8d] R. Kakarla, R. Dulina, N. Hatzenbubler, Y. Hui, M. Sofia, J. Org. Chem. 1996, 61, 8347-8349.
16. [9a] K. S. Ravikumar, F. Barbier, J. P. Bégué, D. Bonnet-Delpon, Tetrahedron 1998, 54, 7457-7464.
17. [9b] K. S. Ravikumar, J P. Bégué, D. Bonnet-Delpon, Tetrahedron Lett. 1998, 39, 3141-3144.
18. [10a] I. T. Horvath, J. Rabai, Science. 1994, 266, 72-75.
19. [10b] R. D. Chambers, G. Sandford, A. Shah, Synth. Commun. 1996, 26, 1861-1866.
20. [10c] I. Klement, H. Lutjens, P. Knochel, Angew. Chem. Int. Ed Engl. 1997, 1454-1456.
21. [10d] A. Ogawa, D. P. Curran, J. Org. Chem. 1997, 62, 450-451 and references cited.
22. L. Eberson, M.P Hartshorn, O. Persson, J. Chem. Soc. Perkin Trans 2, 1995, 1735-1744.
23. [12a] L. Yan, D. Kahne, J. Am. Chem. Soc. 1996, 118, 9239-9248.
24. [12b] D. Crich, S. Sun, J. Am. Chem. Soc. 1997, 119, 11217-11223.
25. T. W. Greene, P. G. M. Wuts (Eds.), Protective Groups in Organic Synthesis, Wiley, New York, 1991, p. 118.
26. J. Drabowicz, M. Mikolajczyk, Synth Commun. 1981, 1025-1030.
27. K. U. Baldenius, H. B. Kagan, Tetrahedron: Asymmetry 1990, 1, 597-610.
28. F. Chen, J. Wan, C. Guan, J. Yang, H. Zhang, Synth. Commun. 1996, 26, 253-260.
29. A. Fabretti, F. Ghelfi, R. Grandi, U. M. Pagnoni, Synth. Commun. 1994, 24, 2393-2398.
30. C. R. Johnson, E. R. Janiga, J. Am. Chem. Soc. 1973, 95, 7692-7700.
31. D. J. Antonjuk, D. D. Ridiey, M. A. Smal, Aust. J. Chem. 1980, 33, 2635-2651
32. R. W. Van der Veenm H. Cerfontain, J Chem. Soc, Perkin Trans. 1 1985, 661-668.
33. T. G. Back, D. L. Baron, K. Yang, J. Org. Chem. 1993, 58, 2407-2413.