Nitric acid in the presence of supported P2O5 on silica gel affords an efficient and mild system for oxidation of organic compounds under solvent-free conditions

Molecular Crystals and Liquid Crystals

Volumn 456, Issue 1, 2006, Pages 85-93

  Hajipour, Abdol R ^a,b   Guo, Lian Wang ^b   Ruoho, Arnold E ^b  

^a ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

^b UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

Author keywords

Is oxidation; Nitric acid; Solvent free; Sulfoxide

Indexed keywords

ALCOHOLS; NITRIC ACID; OXIDATION; SILICA GEL; SOLVENTS;

CARBONYL COMPOUNDS; SOLVENT FREE CONDITIONS; SULFOXIDE;

PHOSPHORUS COMPOUNDS;

EID: 33751548217     PISSN: 15421406     EISSN: 15635287     Source Type: Journal    
DOI: 10.1080/15421400600786363     Document Type: Conference Paper

References (78)

1. Fieser, L. & Fieser, F. M. (1967). Reagent for Organic Synthesis, Wiley: New York, Vol. 1.
2. Sheldon, R. A. & Kkochi, J. K. (1981). Metal-Catalysed Oxidation of Organic Compounds, Academic Press: New York.
3. Ley, S. V., Normann, J., Griffith, W. P., & Marsden, S. P. (1994). Synthesis, 639.
4. Hudlicky, M. (1990). Oxidation in Organic Chemistry, American Chemical Society: Washington, DC.
5. Stevens, R. V., Chapman, K. T., & Walter, H. N. (1980). J. Org. Chem., 45, 2030.
6. Holum, J. R. (1961). J. Org. Chem., 26, 4814.
7. Lee, D. G. (1970). J. Org. Chem., 35, 3589.
8. Highet, R. J. & Wildman, W. C. (1955). J. Am. Chem. Soc., 77, 4399.
9. Carreńo, M. C. (1995), Chem. Rev., 95, 1717.
10. Khurana, J. M., Panda, A. K., & Gogia, A. (1996). Org. Prep. Proced. Int., 28, 234.
11. Orito, K., Hatakeyama, T., Take, M., & Suginome, H. (1995). Synthesis, 1357.
12. Breton, G. W., Fields, J. D., & Kropp, P. J. (1995), Tetrahedron Lett., 36, 3825.
13. (a) Posner, G. H., Weitzberg, M., Hamill, T. G., Asirvatham, E., Cun-Heng, H., & Clardy, J. (1986). Tetrahedron, 42, 2919;
14. (b) Zahouily, M., Journet, M., & Malacria, M. (1994). Synlett., 366;
15. (c) Pyne, S. G. & Hajipour, A. R. (1992). Tetrahedron, 48, 9385;
16. (d) Pyne, S. G., Hajipour, A. R., & Prabakaran, K. (1994). Tetrahedron Lett., 35, 645;
17. (e) Hajipour, A. R. & Hantehzadeh, M. (2000). Phosphorus, Sulfur, and Silicon, 161, 181.
18. (a) Khurana, J. M., Pand, A. K., & Gogia, A. (1996). Org. Prep. Proc. Int., 28, 234;
19. (b) Hajipour, A. R. (1996). Synth. Commun., 26, 3627;
20. (c) Hajipour, A. R. (1997). Indian J. Chem., 36B, 329;
21. (d) Hajipour, A. R. & Pyne, S. G. (1995). J. Chem. Research (S), 360.
22. Hirano, M., Kudo, H., & Morimoto, T. (1992). Bull. Chem. Soc. Jpn., 65, 1744.
23. Hajipour, A. R. (1997). Indian J. Chem., 363, 1069.
24. Hajipour A. R. (1998). Iran J. Sci. Technol., 22, 205.
25. Hirano, M., Yakabe, S., Clark, J. H., Kudo, H., & Morimoto, T. (1996). Synth. Commun., 26, 1875.
26. Ali, M. H. & Stevens, W. C. (1997). Synthesis, 764.
27. Shaabani, A., Teimouri, M. B., & Safaei, H. R. (2000). Synth. Commun., 30, 265.
28. Fraile, J. M., Garcia, J. I., Lazaro, B., & Mayoral, J. A. (1998). Chem. Commun., 1807.
29. Firouzabadi, H., Iranpoor, N., & Zolfigol, M. A. (1998). Synth. Commun., 28, 1179.
30. Drabowicz, J., Midura, W., & Mikolajczyk, M. (1979). Synthesis, 39.
31. Hajipour, A. R., Baltork, I. M., & Kianfar, G. (1999). Indian J. Chem., 38B, 607.
32. (a) Hirano, M., Yakabe, S., Itoh, S., Clark, J. H., & Moromoto, T. (1997). Synthesis, 1161;
33. (b) Hirano, M., Yakabe, S., Clark, J. H., & Morimoto, T. (1996). J. Chem. Soc. Perkin Trans., 1, 2693.
34. Ali, M. H. & Bohnert, G. J. (1998), Synthesis, 1238.
35. (a) Madesclaire, M. (1986). Tetrahedron, 42, 5459;
36. (b) Mata, E. G. (1996). Phosphorus, Sulfur, and Silicon, 117, 231.
37. Hajipour, A. R., Kooshki, B., & Ruoho, A. E. (2005). Tetrahedron Lett., 46, 5503.
38. (a) Ogawa, A., Nishiyama, T., Kambe, N., Murai, S., & Sonada, N.(1987). Tetrahedron Lett, 28, 3271;
39. (b) Johnson, J. R., Bruce, W. P., & Dutcher, J. D. (1943), J. Am. Chem. Soc., 65, 2005.
40. Capozzi, G. & Modena, G. (1974). In: The Chemistry of Thiol Group Part 2, Patai, S. (Ed.), Wiley: New York, 785.
41. (a) Caddick, S. (1995). Tetrahedron, 51, 10403;
42. (b) Michael, D., Mingos, P., & Baghurst, D. R. (1991). Chem. Soc. Rev., 20, 1;
43. (c) Gedye, R. J., Westaway, K., Ali, H., Baldisera, L., Laberge, L., & Rousell, J. (1986). Tetrahedron Lett., 27, 279;
44. (d) Giguere, R. J., Bray, T. L., Duncan, S. M., & Majetich, G. (1986). Tetrahedron Lett., 27, 4945.
45. Abramovitch, A. (1991). Org. Prep. Proc. Int., 23, 685.
46. Loupy,A.,Petit,A.,Ramdiani,M.,Yvanaeff,C.,Majdoud,M.,Labiad,B., &Villemin,D. (1993). Can. J. Chem., 71, 90.
47. (a) Hajipour, A. R., Arbabian, M., & Ruoho, A. E. (2002). J. Org. Chem., 67, 8622.;
48. (b) Hajipour, A. R. & Ruoho, A. E. (2002). Org. Prep. Proced. Int., 34, 647;
49. (c) Hajipour, A. R. & Mazloumi, G. (2002). Synth. Common., 32, 23;
50. (d) Hajipour, A. R. & Ruoho, A. E. (2002). J. Chem. Research (S), 547;
51. (e) Hajipour, A. R., Adibi, H., & Ruoho, A. E. (2003), J. Org. Chem., 68, 4553;
52. (f) Hajipour, A. R., Bageri, H., & Ruoho, A. E. (2004). Bull. Korean Chem. Soc., 25, 1238;
53. (g) Hajipour, A. R. & Malakutikhah, M. (2004). Org. Prep. Proced. Int., 36, 647;
54. (h) Hajipour, A. R. & Ruoho, A. E. (2002). Sulfur Lett., 25, 155;
55. Hajipour, A. R., Mirjalili, B. F., Zarei, A., Khazdooz, L., & Ruoho, A. E. (2004). Tetrahedron Lett., 45, 6607;
56. (j) Hajipour, A. R. & Ruoho, A. E. (2004). J. Iranian Chem. Soc., 1, 159;
57. (k) Hajipour, A. R., Pourmosavi, S. A., & Ruoho, A. E. (2004). J. Sulfur Chemistry, 25, 401;
58. Hajipour, A. R., Zarei, A., Khazdooz, L., Pourmousavi, S. A., Zahmatkesh, S., & Ruoho, A. E. (2004). J. Sulfur Chemistry, 25, 389.
59. (a) Hajipour, A. R., Mallakpour, E., & Imanzadeh, G. (1999). J. Chem. Res., 228;
60. (b) Hajipour, A. R., Mallakpour, E., & Adibi, H. (2000). Chem. Lett., 460;
61. (c) Hajipour, A. R., Mallakpour, E., & Afrousheh, A. (1999). Tetrahedron, 55, 2311;
62. (d) Hajipour, A. R. & Islami, F. (1999). Ind. J. Chem., 38B, 461;
63. (e) Hajipour, A. R., Mallakpour, E., & Imanzadeh, G. (1999). Chem. Lett., 99;
64. (f) Hajipour, A. R. & Hantehzadeh, M. (1999). J. Org. Chem., 64, 8475;
65. (g) Hajipour, A. R., Mallakpour, E., & Backnejad, H. (2000). Synth. Commun., 30, 3855;
66. (h) Hajipour, A. R., Mallakpour, E., & Afrousheh, A. (2000). Phosphorus, Sulfur and Silicon, 160, 67;
67. (i) Hajipour, A. R., Mallakpour, E., & Khoee, S. (2000). Synlett, 740;
68. (j) Hajipour, A. R., Mallakpour, E., & Khoee, S. (2000). Chemistry Lett., 120;
69. (k) Hajipour, A. R., Baltork, I. M., Nikbaghat, K., & Imanzadeh, Gh. (1999). Synth. Commun., 29, 1697.
70. (a) Baltork, I. M., Hajipour, A. R., & Mohammadi, H. (1998). Bull. Chem. Soc. Jpn., 71, 16;
71. (b) Hajipour, A. R. & Mahboobkhah, N. (1998). Synth. Commun., 28, 3143;
72. (c) Hajipour, A. R. & Mahboobkhah, N. (1998). J. Chem. Research (S), 122;
73. (d) Hajipour, A. R., Baltork, I. M., & Kianfar, G. (1998). Bull. Chem. Soc. Jpn., 71, 2655;
74. (e) Hajipour, A. R., Baltork, I. M., & Kianfar, G. (1998). Indian J. Chem., 37B, 607;
75. (f) Hajipour, A. R. & Mahboobkhah, N. (1999). Org. Prep. Proced. Int., 31, 112;
76. (g) Hajipour, A. R., Baltork, I. M., & Niknam, K. (1999). Org. Prep. Proced. Int., 31, 335;
77. (h) Baltork, I. M., Hajipour, A. R., & Haddadi, R. (1999). J. Chem. Research (S), 102;
78. Hajipour, A. R., Mallakpour, E., & Samimi, H. A. (2001). Synlett., 1735.