Montmorillonite K10 catalyzed selective oxidation of sulfides to sulfoxides using hydrogen peroxide

Letters in Organic Chemistry

Volumn 4, Issue 1, 2007, Pages 75-79

  Lakouraj, Moslem Mansour ^a   Tajbakhsh, Mahmood ^a   Tashakkorian, Hamed ^a  

^a UNIVERSITY OF MAZANDARAN   (Iran)

Author keywords

Catalyzed sulfoxidation; Hydrogen peroxide; Montmorillonite K10; Sulfide; Sulfoxide

Indexed keywords

EID: 33947162845     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807780037351     Document Type: Article

References (70)

1. (a) Patei, S.; Rappoport, Z. Chemistry of Sulfoxides and Sulfones, Academic Press: New York, 1988
2. (b) Block, E. Reactions of Organosulfur Compounds, Academic Press: New York, 1978;
3. (c) Holland, H.L. Chem. Rev., 1988, 88, 473
4. (d) Page, P.C.B. Organosulfur Chemistry, I & II, Ed., Springer: Berlin, 1999;
5. (e) Block, E. Angew. Chem. Int. Ed. Engl., 1992, 31, 1135.
6. (a) Folsom, H.E.; Castrillon, J. Synth. Commun., 1992, 22, 1799;
7. (b) Kowalski, P.; Mitka, K.; Ossowska, K.; Kaczorowska, K. Tetrahedron, 2005, 61, 1933;
8. (c) Kaczorowska, K.; Kolarska, Z.; Mitka, K.; Kowalski, P. Tetrahedron, 2005, 61, 8315.
9. (a) Adam, W.; Mitchell, C.M.; Saha-Möller, C.R. Tetrahedron, 1994, 50, 13121;
10. (b) Hajipour, A.R.; Mallakpour, S.E.; Adibi, H. J. Org. Chem., 2002, 67, 8666;
11. (c) Sato, K.; Hyodo, M.; Aoki, M.; Zheng, X.-Q.; Noyori, R. Tetrahedron, 2001, 57, 2469;
12. (d) Mckillop, A.; Tarbin, J.A. Tetrahedron Lett., 1983, 24, 1505;
13. (e) Velusamy, S.; Kumar, A.V.; Saini, R.; Punniyamurthy, T. Tetrahedron Lett., 2005, 46, 3819;
14. (f) Mirkhani, V.; Tangestaninejad, S.; Moghadam, M.; Mohammadpoor-Baltork, I.; Kargar, H.J. J. Mol. Catal. A Chem., 2005, 242, 251;
15. (g) Reich, H.J.; Chow, F.; Peake, S.L. J. Chem. Soc. Chem. Commun., 1978, 299;
16. (h) Stanger, K.J.; Wiench, J.W.; Pruski, M.; Espenson, J.H.; Kraus, G.A.; Angelici, R.J. J. Mol. Catal. A Chem., 2005, 243, 158.
17. (a) Xiong, Z.-X; Huang, N.-P.; Zhong, P. Synth. Commun., 2001, 31, 245;
18. (b) Zincke, T.; Frohneberg, W. Ber. Dtsch. Chem. Ges., 1910, 43, 837;
19. (c) Fries, K.; Vogt, W. Annalen, 1911, 381, 337;
20. (d) Fromm, E. Annalen, 1913, 396, 75;
21. (e) Szmant, H. Organic Sulfur Compounds, Kharasch, N. Ed.; Pergamon Press: New York, 1961, pp. 154;
22. (f) Oae, S.; Onishi, Y.; Kozuka, S.; Tagaki, W. Bull. Chem. Soc. Jpn., 1966, 39, 364;
23. (g) Miotti, U.; Modena, G.; Sedea, L. J. Chem. Soc. (B), 1970, 802;
24. (h) Drabowicz, J.; Midura, W.; Mikolaiczyk, M. Synthesis, 1979, 39;
25. (i) Humffray, A.A.; Imberger, H.E. J. Chem. Soc. Perkin Trans. II, 1981, 382;
26. (j) Kikukawa, K.; Tagaki, W.; Kunieda, N.; Oae, S. Bull. Chem. Soc. Jpn. 1969, 42, 831;
27. (k) Johnson, C.R.; Rigau, J.J. J. Am. Chem. Soc., 1969, 91, 5398;
28. (l) Skattebol, L.; Boulette, B.; Solomon, S. J. Org. Chem., 1967, 32, 3111;
29. (m) Tagaki, W.; Kikukawa, K.; Ando, K.; Oae, S. Chem. Ind., 1964, 38, 1624;
30. (n) Harville, R.; Reed, S.F. J. Org. Chem., 1968, 33, 3976;
31. (o) Tullen, D.L.; Smith, P.J. J. Tenn. Acad. Sci., 1971, 46, 17;
32. (p) Barbieri, G.; Cinquini, M.; Colonna, S.; Montanari, F. J. Chem. Soc. (C), 1968, 659;
33. (q) Traynelis, V.J.; Yoshikawa, Y.; Tarka, S.M. J. Org. Chem., 1973, 38, 3986;
34. (r) Hojo, M.; Masuda, R. Tetrahedron Lett., 1976, 17, 613.
35. Collins, F.M.; Lucy, A.R.; Sharp, C. J. Mol. Catal. A Chem., 1997, 117, 397.
36. (a) Kim, S.S.; Rajagopal, G. Synthesis, 2003, 2461;
37. (b) Phan, Y.D.; Kinch, M.A.; Barker, J.E.; Ren, T. Tetrahedron. Lett., 2005, 46, 397;
38. (c) Hirano, M.; Kudo, H.; Morimoto, T. Bull. Chem. Soc. Jpn., 1994, 67, 1492.
39. Velde, F.V.; Könemann, L.; Rantwijk, F.V.; Sheldon, R.A. Chem. Commun., 1998, 1891.
40. (a) Kannan, P.; Sevvel, R.; Rajagopal, S.; Pitchumani, K.; Srinivasan, C. Tetrahedron 1997, 53, 7635;
41. (b) Hirano, M.; Yakabe, S.; Itoh, S.; Clark, J.H.; Morimoto, T. Synthesis, 1997, 1161;
42. (c) Reddy, T.I.; Varma, R.S.; Chem. Commun., 1997, 471;
43. (d) Ali, M.H.; Leach, D.R.; Schmitz, C.E. Synth. Commun., 1998, 28, 2969.
44. Shirini, F.; Zolfigol, M.A.; Lakouraj, M.M.; Azadbar, M.R. Russ. J. Org. Chem., 2001, 37, 1340.
45. Lakouraj, M.M.; Movassagh, B.; Ghodrati, K. Synth. Commun., 2002, 32, 847.
46. Lakouraj, M.M.; Tajbakhsh, M.; Shirini, F.; Asady Tamami, M.V. Synth. Commun., 2005, 35, 775.
47. Jones, C.W. Applications of Hydrogen Peroxide and Derivatives, Royal Society of Chemistry, Cambridge, 1999.
48. Strukul, G. Catalytic Oxidation with Hydogen Peroxide as Oxidant, Kluwar Academic: Dordrecht, The Netherlands, 1992.
49. Noyori, R.; Aoki, M.; Sato, K. Chem. Commun., 2003, 1977.
50. Drabowicz, J.; Mikojajczyk, M. Synth. Commun., 1981, 11, 1025.
51. Lakouraj, M.M.; Movassagh, B.; Fadaei, Z. Synth. Commun., 2002, 32, 1237.
52. Evans, M.C.W.; Buchanan, B.B.; Arron, D.I. Dictionary of Organic Compound, 6th Ed.; Chapman & Hall, London, 1966.
53. Orito, K.; Hatakeyama, T.; Take, M.; Suginome, H. Synthesis, 1995, 1357.
54. Babieri, G.; Cinquini, M.; Colonna, S.; Montanari, F. J. Chem. Soc., 1968, 659.
55. Colonna, S.; Banfi, S.; Annunziata, R.; Casella, L. J. Org. Chem., 1986, 51, 891.
56. Tsuchiya, Y.; Mori, M.; Taguchi, T.; Yakugaku, Z. Chem. Abstr., 1976, 85, 1422.
57. Crockford, H.D.; Douglas, T.B. J. Am. Chem. Soc., 1934, 56, 1472.
58. Liu, K.T.; Tong, Y.C. J. Org. Chem., 1978, 43, 2717.
59. Seika, S. Aldrich Catalog Handbook of Fine Chemicals, Aldrich Co., 1991.
60. Fabretti, A.; Ghelti, F.; Grandi, R.; Pagnoni, U.M. Synth. Commun., 1994, 24, 2393.
61. Raton, B. Handbook of Chemistry and Physics, 70th Ed.; CRC press: USA, 1990.
62. Varma, R.S.; Dahiya, R. Synth. Commun., 1998, 28, 4087.
63. Sasaki, Y.; Ushimaru, K.; Iteya, K.; Nakayama, H.; Yamaguchi, S.; Ichihara, J. Tetrahedron Lett., 2004, 45, 9513.
64. Yang, R.-Y.; Dai, L.-X. Synth. Commun., 1994, 24, 2229.
65. Song, G.; Wang, F.; Zhang, H.; Lu, X.; Wang, C. Synth. Commun., 1998, 28, 2783.
66. Fringuelli, F.; Pellegrino, R.; Pizzo, F. Synth. Commun., 1993, 23, 3157.
67. Mashraqui, S.H.; Mudaliar, C.D.; Karnik, M.A. Synth. Commun., 1998, 28, 939.
68. Ali, M.H.; Stevens, W.C. Synthesis, 1997, 764.
69. Santaniello, E.; Manzocchi, A.; Farachi, C. Chem. Commun., 1980, 563.
70. Reddy, T.I.; Varma, R.S. Chem. Commun., 1997, 471.