1,1,1-Trifluoroacetone as an efficient catalyst for the hydrogen peroxide promoted selective oxidation of sulfides to sulfoxides

Synthetic Communications

Volumn 27, Issue 3, 1997, Pages 441-446

  Lupattelli, Paolo ^a   Ruzziconi, Renzo ^a   Scafato, Patrizia ^a   Degl'Innocenti, Alessandro ^b   Paolobelli, Anna Belli ^c  

^a UNIVERSITY OF BASILICATA   (Italy)

^b Dipartimento di Chimica   (Italy)

^c UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

SULFOXIDE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; OXIDATION; REACTION ANALYSIS;

EID: 0030981975     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919708006045     Document Type: Article

References (21)

1. Solladie, G. in "Comprehensive Organic Synthesis" Trost, B.M.; Fleming, L., Ed., 1991, Vol. 6, p. 148. Fleming, I. Chem.Ind. (London), 1975, 449. Block, E. J.Chem.Ed. 1971, 48, 814.
2. Solladie, G. in "Comprehensive Organic Synthesis" Trost, B.M.; Fleming, L., Ed., 1991, Vol. 6, p. 148. Fleming, I. Chem.Ind. (London), 1975, 449. Block, E. J.Chem.Ed. 1971, 48, 814.
3. Solladie, G. in "Comprehensive Organic Synthesis" Trost, B.M.; Fleming, L., Ed., 1991, Vol. 6, p. 148. Fleming, I. Chem.Ind. (London), 1975, 449. Block, E. J.Chem.Ed. 1971, 48, 814.
4. See for example: a) Mlochowski, J.; Giurg, M.; Kubicz, E.; Said, S.B. Synth.Commun. 1996, 26, 291. b) Chen, F.; Wan, J.L.; Guan, C.; Yang, J.; Zhang, H. Synth.Commnn. 1996, 26, 253. c) Jorgensen, K.A. J.Chem.Soc. Perkin Trans. II 1994, 117. d) Bethell, D.; Graham, A.E.; Heer, J.P.; Markopoulou, O.; Page, P.C.B.; Park, B.K. J.Chem.Soc. Perkin Trans. II 1993, 2161. e) Page, P.C.B.; Graham, A.E.; Bethell, D.; Park, B.K. Synth.Commun. 1993, 23, 1507. f) For a review see also Drabowicz, J.; Kielbasinski, P.; Mikolajczyk in "The Chemistry of Sulphones and sulphoxides", Patai, S.; Rappoport, Z.; Stirling, C.J., Ed.; John Wiley & sons Ltd. 1988, Chapter 8.
5. See for example: a) Mlochowski, J.; Giurg, M.; Kubicz, E.; Said, S.B. Synth.Commun. 1996, 26, 291. b) Chen, F.; Wan, J.L.; Guan, C.; Yang, J.; Zhang, H. Synth.Commnn. 1996, 26, 253. c) Jorgensen, K.A. J.Chem.Soc. Perkin Trans. II 1994, 117. d) Bethell, D.; Graham, A.E.; Heer, J.P.; Markopoulou, O.; Page, P.C.B.; Park, B.K. J.Chem.Soc. Perkin Trans. II 1993, 2161. e) Page, P.C.B.; Graham, A.E.; Bethell, D.; Park, B.K. Synth.Commun. 1993, 23, 1507. f) For a review see also Drabowicz, J.; Kielbasinski, P.; Mikolajczyk in "The Chemistry of Sulphones and sulphoxides", Patai, S.; Rappoport, Z.; Stirling, C.J., Ed.; John Wiley & sons Ltd. 1988, Chapter 8.
6. See for example: a) Mlochowski, J.; Giurg, M.; Kubicz, E.; Said, S.B. Synth.Commun. 1996, 26, 291. b) Chen, F.; Wan, J.L.; Guan, C.; Yang, J.; Zhang, H. Synth.Commnn. 1996, 26, 253. c) Jorgensen, K.A. J.Chem.Soc. Perkin Trans. II 1994, 117. d) Bethell, D.; Graham, A.E.; Heer, J.P.; Markopoulou, O.; Page, P.C.B.; Park, B.K. J.Chem.Soc. Perkin Trans. II 1993, 2161. e) Page, P.C.B.; Graham, A.E.; Bethell, D.; Park, B.K. Synth.Commun. 1993, 23, 1507. f) For a review see also Drabowicz, J.; Kielbasinski, P.; Mikolajczyk in "The Chemistry of Sulphones and sulphoxides", Patai, S.; Rappoport, Z.; Stirling, C.J., Ed.; John Wiley & sons Ltd. 1988, Chapter 8.
7. See for example: a) Mlochowski, J.; Giurg, M.; Kubicz, E.; Said, S.B. Synth.Commun. 1996, 26, 291. b) Chen, F.; Wan, J.L.; Guan, C.; Yang, J.; Zhang, H. Synth.Commnn. 1996, 26, 253. c) Jorgensen, K.A. J.Chem.Soc. Perkin Trans. II 1994, 117. d) Bethell, D.; Graham, A.E.; Heer, J.P.; Markopoulou, O.; Page, P.C.B.; Park, B.K. J.Chem.Soc. Perkin Trans. II 1993, 2161. e) Page, P.C.B.; Graham, A.E.; Bethell, D.; Park, B.K. Synth.Commun. 1993, 23, 1507. f) For a review see also Drabowicz, J.; Kielbasinski, P.; Mikolajczyk in "The Chemistry of Sulphones and sulphoxides", Patai, S.; Rappoport, Z.; Stirling, C.J., Ed.; John Wiley & sons Ltd. 1988, Chapter 8.
8. See for example: a) Mlochowski, J.; Giurg, M.; Kubicz, E.; Said, S.B. Synth.Commun. 1996, 26, 291. b) Chen, F.; Wan, J.L.; Guan, C.; Yang, J.; Zhang, H. Synth.Commnn. 1996, 26, 253. c) Jorgensen, K.A. J.Chem.Soc. Perkin Trans. II 1994, 117. d) Bethell, D.; Graham, A.E.; Heer, J.P.; Markopoulou, O.; Page, P.C.B.; Park, B.K. J.Chem.Soc. Perkin Trans. II 1993, 2161. e) Page, P.C.B.; Graham, A.E.; Bethell, D.; Park, B.K. Synth.Commun. 1993, 23, 1507. f) For a review see also Drabowicz, J.; Kielbasinski, P.; Mikolajczyk in "The Chemistry of Sulphones and sulphoxides", Patai, S.; Rappoport, Z.; Stirling, C.J., Ed.; John Wiley & sons Ltd. 1988, Chapter 8.
9. See for example: a) Mlochowski, J.; Giurg, M.; Kubicz, E.; Said, S.B. Synth.Commun. 1996, 26, 291. b) Chen, F.; Wan, J.L.; Guan, C.; Yang, J.; Zhang, H. Synth.Commnn. 1996, 26, 253. c) Jorgensen, K.A. J.Chem.Soc. Perkin Trans. II 1994, 117. d) Bethell, D.; Graham, A.E.; Heer, J.P.; Markopoulou, O.; Page, P.C.B.; Park, B.K. J.Chem.Soc. Perkin Trans. II 1993, 2161. e) Page, P.C.B.; Graham, A.E.; Bethell, D.; Park, B.K. Synth.Commun. 1993, 23, 1507. f) For a review see also Drabowicz, J.; Kielbasinski, P.; Mikolajczyk in "The Chemistry of Sulphones and sulphoxides", Patai, S.; Rappoport, Z.; Stirling, C.J., Ed.; John Wiley & sons Ltd. 1988, Chapter 8.
10. Ref. 2f, pp. 236-240.
11. Hinsberg, O. Chem.Ber. 1908, 41, 2836. See also Cerniani, A.; Modena, G.; Todesco, P.E. Gazz.Chim.It. 1960, 90, 382.
12. Hinsberg, O. Chem.Ber. 1908, 41, 2836. See also Cerniani, A.; Modena, G.; Todesco, P.E. Gazz.Chim.It. 1960, 90, 382.
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15. Onto, K.; Hatakeyama, T.; Takeo, M.; Suginome, H. Synthesis 1995, 1357. Tsuchihashi, G.; Ogura, K. D.O.S. 2336817 (1974); Chem.Abstr. 1974, 80, 108182.
16. Onto, K.; Hatakeyama, T.; Takeo, M.; Suginome, H. Synthesis 1995, 1357. Tsuchihashi, G.; Ogura, K. D.O.S. 2336817 (1974); Chem.Abstr. 1974, 80, 108182.
17. Watanabe, Y.; Numata, T.; Oae, S. Synthesis 1981, 204.
18. Drabowicz, J.; Mikolajczyk, M. Synthesis 1978, 758. Reich, H.J.; Chow, F. Peake, S.L. Synthesis 1978, 299.
19. Drabowicz, J.; Mikolajczyk, M. Synthesis 1978, 758. Reich, H.J.; Chow, F. Peake, S.L. Synthesis 1978, 299.
20. 2 at -60°C, the stoichiometric amount of this oxidant has to be used in order to obtain a good yield of sulfoxide without over-oxidation products.
21. Ganem, B.; Biloski, A.J.; Heggs, R.P. Tetrahedron Lett. 1980, 21, 689.