Oxidation of sulfides to sulfoxides. Part 2: Oxidation by hydrogen peroxide

Tetrahedron

Volumn 61, Issue 35, 2005, Pages 8315-8327

  Kaczorowska, Katarzyna ^a   Kolarska, Zofia ^a   Mitka, Katarzyna ^b   Kowalski, Piotr ^a,b  

^a Pharmaceutical Company   (Poland)

^b CRACOW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Hydrogen peroxide; Oxidation; Sulfides; Sulfoxides

Indexed keywords

HYDROGEN PEROXIDE; IRON; MOLYBDENUM; RHENIUM; SELENIUM; SOLVENT; SULFIDE; SULFOXIDE; TELLURIUM; TITANIUM; TUNGSTEN; VANADIUM;

CATALYSIS; CATALYST; CHEMICAL REACTION; OXIDATION; PRIORITY JOURNAL; REVIEW;

EID: 23044466213     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.05.044     Document Type: Review

References (120)

1. D.Mc. Tavish, M.M. Buckley, and R.C. Heel Drugs 1 1991 138 170
2. S. Okabe, and K. Shimosako J. Physiol. Pharmacol. 52 2001 639 656
3. C.M. Spencer, and D. Faulds Drugs 60 2000 321 329
4. P. Richardson, Ch.J. Hawkey, and W.A. Stack Drugs 56 1998 307 335
5. M. Salas, A. Ward, and J. Caro BMC Gastroenterol. 2 2002 17
6. K.C. Lai, S.K. Lam, K.M. Chu, B.C. Wong, W.M. Hui, W.H. Hu, G.K. Lau, W.M. Wong, M.F. Yuen, A.O. Chan, C.L. Lai, and J. Wong N. Engl. J. Med. 346 2002 2033 2038
7. D.E. Baker Rev. Gastroenterol. Disord. 1 2001 32 41
8. M. Sovova, and P. Sova Ceska Slov. Farm. 52 2003 82 87
9. M.A. Adetumjbi, and B.H. Lau Med. Hypotheses 12 2000 222 237
10. M. Focke, A. Feld, and K. Lichtenthaler FEBS Lett. 12 1990 106 108
11. K.C. Agarwal Med. Res. 16 1996 111 124
12. C. Perez-Giraldo, G. Cruz-Villalon, R. Sanchez-Silos, R. Martinez-Rubio, M.T. Blanco, and A.C. Gomez-Garcia J. Appl. Microbiol. 95 2003 709 711
13. S. Yoshida, S. Kasuga, N. Hayashi, T. Ushiroguchi, H. Matsuura, and S. Nakagawa Appl. Environ. Microbiol. 53 1987 615 617
14. E. Inoue, E. Komoto, Y. Taniyama, and S. Mitsuhashi Jpn. J. Antibiot. 49 1996 338 351
15. G. Merino, A.J. Molina, J.L. Garcia, M.M. Pulido, J.G. Prieto, and A.I. Alvarez J. Pharm. Pharmacol. 55 2003 757 764
16. M.T. Teruel, A.E. Felipe, H.D. Solana, J.M. Sallovitz, and C.E. Lanusse Vet. Hum. Toxicol. 45 2003 131 136
17. B. Kotelanski, R.J. Grozmann, and J.N. Cohn Clin. Pharmacol. Ther. 14 1973 427 433
18. W.J. Parsons, V. Ramkumar, and G.L. Stiles Am. Soc. Pharmacol. Exp. Ther. 1988 761 768
19. R. Schmied, G.X. Wang, and M. Korth Circ. Res. 68 1991 597 604
20. F. Lechin, B. Van der Dijs, B. Pardey-Maldonado, E. John, V. Jimenez, B. Orozco, S. Baez, and M.E. Lechin J. Med. 31 2000 333 361
21. U.A. Zifko, M. Rupp, S. Schwarz, H.T. Zipko, and E.M. Maida J. Neurol. 249 2002 983 987
22. A.V. Nieves, and A.E. Lang Clin. Neuropharmacol. 25 2002 111 114
23. S. Padmanabhan, R.C. Lavin, and G.J. Durant Tetrahedron: Asymmetry 11 2000 3455 3457
24. C.W. Jones Applications of Hydrogen Peroxide and Derivatives 1999 Royal Society of Chemistry Cambridge
25. G. Strukul Catalytic Oxidations with Hydrogen Peroxide as Oxidant 1992 Kluwer Academic Dordrecht, The Netherlands
26. K. Sato, M. Hyodo, M. Aoki, X.-Q. Zheng, and R. Noyori Tetrahedron 57 2001 2469 2476
27. E. Dumitriu, C. Guimon, A. Cordoneanu, S. Casenave, T. Hulea, C. Chelaru, H. Martinez, and V. Hulea Catal. Today 66 2001 529 534
28. R. Noyori, M. Aoki, and K. Sato Chem. Commun. 2003 1977 1986
29. J.M. Fraile, J.I. Garcia, B. Lázaro, and J.A. Mayoral Chem. Commun. 1998 1807 1808
30. V. Hulea, F. Fajula, and J. Bousquet J. Catal. 198 2001 179 186
31. V. Hulea, P. Moreau, and F. Di Renzo J. Mol. Catal. 111 1996 325 332
32. O. Bortolini, F. Di Furia, G. Modena, and R. Seraglia J. Org. Chem. 50 1985 2688 2690
33. Berenguer, M. R.; Campon, P. J.; Coppi L. EP Patent 1270555A1; Chem. Abstr. 2003, 135, 242230.
34. Oguma, J.; Hagiya, K.; Miyawaki, T. EP Patent 1334956A2; Chem. Abstr. 2002, 136, 164701.
35. Hashimoto, H.; Urai, T. EP Patent 1277752A1; Chem. Abstr. 2003, 135, 357923.
36. Cotton, H. WO Patent 99/25711; Chem. Abstr. 2000, 131, 5258y.
37. 1.
38. M. Madesclaire Tetrahedron 42 1986 5459 5495
39. R.S. Reddy, J.S. Reddy, R. Kumar, and P. Kumar J. Chem. Soc., Chem. Commun. 84-85 1992 5270
40. M. Gazdar, and S. Smiles J. Chem. Soc. 93 1908 1833
41. Methoden der Organischen Chemie (Houben-Weyl), 1955; Vol. IX, pp 211-221.
42. R. Pummerer Chem. Ber. 43 1910 1406
43. P. Karrer, E. Scheitlin, and H. Siegrist Helv. Chim. Acta 33 1950 1237
44. W. Steinkopf, J. Herold, and J. Stohr Chem. Ber. 53 1920 1007
45. S. Hunig, and O. Boes Liebigs Ann. Chem. 579 1953 23
46. J. Loevenich, and B. Mitarbb Liebigs Ann. Chem. 62 1929 3084
47. A.C. Cope, D.E. Morrison, and L. Field J. Am. Chem. Soc. 72 1950 59
48. R.L. Shriner, H.C. Struck, and W.J. Jorison J. Am. Chem. Soc. 52 1930 2060
49. O. Hinsberg J. Prakt. Chem. 85 1912 337
50. J.A. Smythe J. Chem. Soc. 101 1930 2076
51. E.E.V. Bell, and G. McDonald Benett J. Chem. Soc. 1928 3189
52. J. Drabowicz, and M. Mikołajczyk Synth. Commun. 11 1981 1025
53. S. Patai, Z. Rappoport, and Ch. Stirling The Chemistry of Sulphones and Sulphoxides 1988 Wiley Chichester, UK pp 233-378
54. W.L. Xu, Y.L. Zheng, Q.S. Zhang, and H.S. Zhu Synthesis 2 2004 0227 0232
55. K.S. Ravikumar, J.P. Begue, and D. Bonnet-Delpon Tetrahedron Lett. 39 1998 3141 3144
56. Ch. Ohta, H. Shimizu, A. Kondo, and T. Katsuki Synlett 1 2002 161 163
57. W. Adam, M.N. Korb, K.J. Roschmann, S. Moeller, and R. Chantu J. Org. Chem. 63 1998 103423 103428
58. B. Pelotier, M.S. Anson, I.B. Campbell, S.J.F. Macdonald, G. Priem, and R.F.W. Jackson Synlett 7 2002 1055 1060
59. Masayasu, K.; Yoshio, T.; Norio, I. EP Patent 0302720B1; Chem. Abstr. 1989, 111, 39369n.
60. F.E. Hardy, P.R.H. Speakman, and P. Robson J. Chem. Soc. (C) 1969 2334
61. A.V. Anisimov, E.V. Fedorova, A.Z. Lesnugin, V.M. Senyavin, L.A. Aslanov, V.B. Rybakov, and A.V. Tarakanova Catal. Today 78 2003 319 325
62. Slemon, C.; Macel, B. WO Patent 95/12590; Chem. Abstr. 1995, 122, 133189c.
63. Slemon, C.; Macel, B. US Patent 5502195; Chem. Abstr. 1995, 122, 133189c.
64. J. Skarżewski, E. Wojaczyńska, and I. Turowska-Tyrk Tetrahedron: Asymmetry 13 2002 369 375
65. J. Skarżewski, E. Ostrycharz, and R. Siedlecka Tetrahedron: Asymmetry 10 1999 3457 3461
66. Gama, Á.; Flores-López, L.Z.; Aguirre, G.; Parra-Hake M.; Hellberg L.H.; Somanathan R. ARKIVOC 2003, (xi), 4-15.
67. C. Bolm, and F. Bienewald Angew. Chem., Int. Ed. Engl. 34 1995 2640 2642
68. C. Bolm, G. Schlingloff, and F. Bienewald J. Mol. Catal. A: Chem. 117 1997 347 350
69. T.P. Tang, S.K. Volkman, and J.A. Ellman J. Org. Chem. 66 2001 8772 8778
70. F. Yuste, B. Ortiz, A. Carrasco, M. Peralta, L. Quintero, R. Sanchez-Obregon, F. Walls, and J.L.G. Ruano Tetrahedron: Asymmetry 11 2000 3079 3090
71. N.N. Karpyshev, O.D. Yakovleva, E.P. Talsi, K.P. Bryliakov, O.V. Tolstikova, and A.G. Tolstikov J. Mol. Catal. 157 2000 91 95
72. A.H. Vetter, and A. Berkessel Tetrahedron Lett. 39 1998 1741
73. J.H. Espenson Chem. Commun. 1999 479 488
74. W. Adam, C.M. Mitchell, and Ch.R. Saha-Möller Tetrahedron 50 1994 13121 13124
75. C.C. Romao, F.E. Khun, and W.A. Herrmann Chem. Rev. 97 1997 3197 3246
76. W.A. Herrman, R.W. Fischer, M.U. Rauch, and W. Scherer J. Mol. Catal. 86 1994 243 266
77. J. Bringsma, R. La Crois, B.L. Feringa, M.J. Donnoli, and C. Rosini Tetrahedron Lett. 42 2001 4049 4052
78. H.Q.N. Gunaratne, M.A. McKervey, S. Feutren, J. Finlay, and J. Boyd Tetrahedron Lett. 39 1998 5655 5658
79. Y. Watanabe, T. Numata, and S. Oae Synthesis 1981 204
80. D.J. Robinson, L. Davies, N. McGuire, D.F. Lee, P. McMorn, D.J. Willock, G.W. Watson, P.P.C. Bulman, D. Bethell, and G.J. Hutchings Phys. Chem. Chem. Phys. 2 2000 1523 1529
81. P.S. Raghavan, V. Ramaswamy, T.T. Upadhya, A. Sudalai, A.V. Ramaswamy, and S. Sivasanker J. Mol. Catal. A: Chem. 122 1997 75 80
82. S.V.N. Raju, T.T. Upadhya, S. Ponatnam, T. Daniel, and A. Sudalai Chem. Commun. 1996 1969
83. P. Moreau, V. Hulea, S. Gomez, D. Brunel, and F.D. Renzo Appl. Catal. A: General 155 1997 253 263
84. A. Corma, M. Iglesias, and F. Sánchez Catal. Lett. 39 1996 153
85. M. Iwamoto, Y. Tanaka, J. Hirosumi, N. Kita, and S. Triwahyono Microporous Mesoporous Mater. 48 2001 271 277
86. O.A. Kholdeeva, A.Y. Derevyankin, A.N. Shmakov, N.N. Trukhan, E.A. Paukshtis, A. Tuel, and V.N. Romannikov J. Mol. Catal. A: Chem. 158 2000 417 421
87. T. Tatsumi, M. Nakamura, K. Yuasa, and H. Tominaga Catal. Lett. 10 1991 259
88. R.C. Huybrechts, L.De. Bruycker, and P.A. Jacobs Nature 1990 240
89. P. Pitchen, E. Dunach, M.N. Deshmukh, and H.B. Kagan J. Am. Chem. Soc. 106 1984 81 88
90. S.D. Green, Ch. Monti, R.F.W. Jackson, M.S. Anson, and S.J.F. Macdonald Chem. Commun. 2001 2594 2595
91. Buxade Vinas, A. ES Patent 2060541A1; Chem. Abstr. 1995, 123, 228183f.
92. W. Winter, C. Mark, and V. Schurig Inorg. Chem. 19 1980 2045 2048
93. M. Bonchio, T. Carofiglio, F. Di Furia, and R. Fornasier J. Org. Chem. 60 1995 5986 5988
94. O. Bortolini, F.D. Furia, G. Modena, and C. Scardellato J. Mol. Catal. 11 1981 107
95. Palomo Coll, A. WO Patent 02/28852 A1; Chem. Abstr. 2002, 136, 294832m.
96. P.R.H.P. Rao, A.A. Belhekar, S.G. Hegde, A.V. Ramaswamy, and P. Ratnasamy J. Catal. 141 1993 595
97. N.K. Mal, V. Ramaswamy, S. Ganapathy, and A.V. Ramaswamy J. Chem. Commun. 1994 1933
98. T. Sen, V. Ramaswamy, S. Ganapathy, P.R. Rajamohanan, and S. Sivasanker J. Phys. Chem. 100 1996 3809
99. P.S.E. Dai, and J.H. Lunsford J. Catal. 64 1980 173
100. F. Batigalhia, M. Zaldini-Hernandes, A.G. Ferreira, I. Malvestit, and Q.B. Cass Tetrahedron 57 2001 9669 9676
101. K.S. Kim, H.J. Hwang, Ch.S. Cheong, and Ch.S. Hahn Tetrahedron Lett. 31 1990 2893 2894
102. J. Drabowicz, and M. Mikołajczyk Synthesis 1978 758
103. R.D. Chambers, and M. Clark Tetrahedron Lett. 1970 2741
104. R.P. Heggs, and B. Ganem J. Am. Chem. Soc. 101 1979 2484
105. B. Ganem, R.P. Heggs, A.J. Biloski, and D.R. Schwartz Tetrahedron Lett. 21 1980 685 689
106. A. Arcoria, F.P. Ballistreri, G.A. Tomaselli, F.D. Furia, and G. Modena J. Mol. Catal. 24 1984 189
107. Freyermuth Harlen, B.; Buc Saul, R. US Patent 3006963.
108. H.S. Schultz, H.B. Freyermuth, and S.R. Buc J. Org. Chem. 28 1963 1140 1142
109. A. Arcoria, F.P. Ballistreri, G.A. Tomaselli, F.D. Furia, and G. Modena J. Mol. Catal. 18 1983 177
110. Palomo Coll, A. ES Patent 2105953; Chem. Abstr. 1994, 120, 107017j.
111. Y. Ishii, H. Tanaka, and Y. Nisiyama Chem. Lett. 1994 1 4
112. Z. Stec, J. Zawadiak, A. Skibinski, and G. Pastuch Pol. J. Chem. 70 1996 1121 1123
113. R. Neumann, and D. Juwiler Tetrahedron 52 1996 8781 8788
114. N.M. Gresley, W.P. Griffith, A.C. Laemmel, H.I.S. Nogueira, and B.C. Parkin J. Mol. Catal. 117 1997 185 198
115. F.M. Collins, A.R. Lucy, and C. Sharp J. Mol. Catal. 117 1997 397 403
116. V.V. Thakur, and A. Sudalai Tetrahedron: Asymmetry 14 2003 407 410
117. Jang, J. M.; Kim, M. H. WO Patent 02074766; Chem. Abstr. 2002, 137, 263030.
118. J. Legros, and C. Bolm Angew. Chem., Int. Ed. 42 2003 5487 5489
119. C. Duboc-Toia, S. Měnage, C. Lambeaux, and M. Fontecave Tetrahedron Lett. 38 1997 3727 3730
120. P. Kowalski, K. Mitka, K. Ossowska, and Z. Kolarska Tetrahedron 61 2005 1933 1953