Fluorous biphasic catalytic oxidation of sulfides by molecular oxygen/2,2-dimethylpropanal

European Journal of Organic Chemistry

Volumn , Issue 1, 2001, Pages 181-186

  Colonna, Stefano ^a   Gaggero, Nicoletta ^a   Montanari, Fernando ^b   Pozzi, Gianluca ^b   Quici, Silvio ^b  

^a Facolta di Farmacia   (Italy)

^b CNR   (Italy)

Author keywords

Biphasic catalysis; Cobalt; Oxidations; Phthalocyanines; Porphyrinoids

Indexed keywords

COBALT; PIVALDEHYDE; PROPIONALDEHYDE; SULFIDE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COMPLEX FORMATION; OXIDATION; SYNTHESIS;

EID: 0035133242     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200101)2001:1<181::AID-EJOC181>3.0.CO;2-3     Document Type: Article

References (44)

1. [1a] I. T. Horváth, J. Rábai, Science 1994, 266, 72-75;
2. [1b] I .T. Horváth, Acc. Chem. Res. 1998, 31, 641-650.
3. [1c] R. Fish, Chem. Eur J. 1999, 5, 1677-1680 -
4. [1d] E. De Wolf, G. van Koten, B.-J. Deelman, Chem. Soc. Rev. 1999, 28, 37-41.
5. [1e] M. Cavazzini, F. Montanari, G. Pozzi, S. Quici, J. Fluorine Chem. 1999, 94, 183-193.
6. J. A. Gladysz, Science 1994, 266, 55-56.
7. [3a] G. Pozzi, F. Montanari, S. Quici, Chem. Commun. 1997, 69-70.
8. [3b] G. Pozzi, M. Cavazzini, S. Quici, S. Fontana, Tetrahedron Lett. 1997, 38, 7605-7608.
9. [3c] G. Pozzi, F. Cinato, F. Montanari, S. Quici, Chem. Commun. 1998, 877-878.
10. [3d] G. Pozzi, M. Cavazzini, F. Cinato, F. Montanari, S. Quici, Eur. J. Org. Chem. 1999, 1947-1955.
11. J. Drabowicz, P. Kielbasinski, M. Mikolajczik, The Chemistry of Sulfones and Sulfoxides (Eds.: S. Patai, Z. Rappoport, C. J. M. Stirling), Wiley, New York, 1988, p. 233.
12. For recent developments see: [5a] S. Colonna, N. Gaggero, C. Richelmi, P. Pasta, Trends Biotech. 1999, 17, 163-168.
13. [5b] S. Colonna, N. Gaggero, P. Pasta, G. Ottolina, Chem. Commun. 1996, 2303-2307.
14. I. T. Horváth, J. Rábai (Exxon Comp.), U.S. Pat. 5,463,082, 1995; Chem. Abstr. 1995, 123, 87349a.
15. I. Klement, H. Lütjens, P. Knochel, Angew. Chem. 1997, 109, 1603-1605;
16. Angew. Chem. Int. Ed. Engl. 1997, 36, 1454-1456.
17. [8a] K. S. Ravikumar, J.-P. Bégué, D. Bonnet-Delpon, Tetrahedron Lett. 1998, 39, 3141-3144.
18. [8b] K. S. Ravikumar, Y. M. Zhang, J.-P. Bégué, D. Bonnet-Delpon, Eur. J. Org. Chem. 1998, 2937-2940.
19. [9a] Metalloporphyrin-catalyzed oxidations (Eds. F. Montanari, L. Casella), Kluwer, Dordrecht, 1994.
20. [9b] Metalloporphyrins in catalytic oxidations (Ed. R. A. Sheldon), Marcel Dekker, New York, 1994.
21. [9c] A. Marques, M. di Matteo, M.-F. Ruasse, Can. J. Chem. 1998, 76, 770-775 and references therein cited.
22. D. P. Curran, Angew. Chem. 1998, 110, 1230-1255;
23. Angew. Chem. Int. Ed. 1998, 37, 1175-1196 and references cited therein.
24. J. S. Lindsey, I. C. Schreiman, H. C. Hsu, P. C. Kearney, A. M. Marguerettaz, J. Org. Chem. 1987, 52, 827-836.
25. Phthalocyanines - Properties and Applications (Eds. C. C. Leznoff, A. B. P. Lever), VCH, Weinheim, 1993.
26. T. M. Keller, J. R. Griffith, J. Fluorine Chem. 1978, 12, 73-77.
27. R. P. Linstead, P. A. Barrett, C. S. Dent, J. Chem. Soc. 1936, 1719-1737.
28. L. P. Barthel-Rosa, J. A. Gladysz, Coord. Chem. Rev. 1999, 192, 587-605.
29. M. M. dell'Anna, P. Mastrorilli, C. F. Nobile, J. Mol. Catal. A, Chem. 1996, 108, 57-62 and references cited therein.
30. G. Song, F. Wang, H. Zhang, X. Lu, C. Whang, Synth. Commun. 1998, 28, 2783-2787.
31. Y. Gaigneaux, R. Maggi, P. Ruiz, B. Delmon, J. Mol. Catal. A, Chem. 1996, 109, 67-74.
32. A. Wolberg, J. Manassen, J. Am. Chem. Soc. 1970, 92, 2982-2991.
33. [20a] Y. Watanabe, T. Numata, S. Oae, Tetrahedron Lett. 1980, 21, 3685-3688.
34. [20b] S. Oae, Y. Watanabe, T. Iyanari, Tetrahedron Lett. 1982, 23, 533-536.
35. [20c] S. Oae, Y. Watanabe, K. Fujimori, Tetrahedron Lett. 1982, 23, 1189-1192.
36. [21a] E. Baciocchi, O. Lanzalunga, F. Marconi, Tetrahedron Lett. 1994, 35, 9771-9774. -
37. [21b] E. Baciocchi, M. Ioele, O. Lanzalunga, M. Malandrucco, S. Steenken, J. Am. Chem. Soc. 1996, 118, 8973-8974.
38. [21c] E. Baciocchi, O. Lanzalunga, B. Pirozzi, Tetrahedron 1997, 53, 12287-12298.
39. W. Nam, H. J. Kim, S. H. Kim, R. Y. N. Ho, J. S. Valentine, Inorg. Chem. 1996, 35, 1045-1049.
40. F. Montanari, S. Banfi, G. Pozzi, S. Quici, Rev. Heteroatom Chem. 1992, 6, 94-141 and references cited therein.
41. A. Pentilla, C. R. Boyle, M. L. Salin, Biochem. Biophys. Res. Commun. 1996, 226, 135-139.
42. J. Haber, T. Mlodnicka, J. Mol. Cat. 1992, 74, 131-141 and references cited therein.
43. T. Mukaiyama, T. Yamada, Bull. Chem. Soc. Jpn. 1995, 68, 17-35 and references cited therein.
44. G. Pozzi, I. Colombani, M. Miglioli, F. Montanari, S. Quici, Tetrahedron 1997, 53, 6145-6162.