A Solvent Free Route to the Synthesis of Diaryl Sulfoxides

Document Type : Research Article

Authors

Teacher Training University, Postal Code 15614, Tehran, I. R. IRAN

Abstract

The solvent free route for the synthesis of diaryl sulfoxides from arenes and thionyl chloride in the presence of Lewis acids such as aluminum chloride and ferric chloride on silica gel are described.

Keywords

Main Subjects

References

 

[1] (a) Holland, H. L. Chem. Rev., 88, 473 (1988); (b) Block, E., Angew.  Chem. Int.  Ed. En., 31, 1135  (1992); (c) Edline Lucien and Alexander Greer, J. Org. Chem., 66, 4576 (2001).
[2] Soladie, G., Synthesis, 185(1981).
[3] (a) Carreno, M. C., Chem. Rev., 95, 1717 (1995); (b) Davis, S. G., Loveridge, T., Clugh, J. M., Synlett, 66 (1997).
[4] Magnus, P. D., Tetrahedron, 33, 2019 (1977); (b) Review: Madesclaire, M., Tetrahedron, 44, 6537 (1988).
[5] Yamamoto, K., Miyatake, K., Nishimura, Y., Tsuchida, E., Chem. Commun., 2099 (1996).
[6] Crivello, J. V., Lam, J. H. W., Macromolecules, 10, 1307 (1977).
[7] Miller, R. D., Renaldo, A. F., Ito, J., J. Org. Chem., 53, 5571 (1988).
[8] (a) Gazdar, M., Smiles, S., J. Chem. Soc., 97, 2248 (1910); (b) Gump, W. S., Vitucci, J. C., J. Am. Chem. Soc., 67, 238 (1945); (c) Jung, M. E., Jachiet, D., Khan,  S. I.  and Kim, C., Tetrahedron Lett., 36, 361 (1995); (d) Mohile, S. J., Potdar, M. K., Salunkhe, M. M., Tetrahedron Lett., 44, 1255 (2003).[9]  (a) Khurana,  J.  M.,  Panda,  A.  K.,  Gogia, A., Org.  Prep. Proced. Int ., 28, 234 (1996); (b) Orito, K., Hatakeyama, T., Take, M., Suginome, H., Synthesis, 1357 (1995); (c) Breton, G. W., Fields, J. D., Kropp, P. J., Tetrahedron Lett., 36, 3825 (1995); (d) Hirano, M., Kudo, H., Morimoto, T., Bull. Chem. Soc. Jpn., 67, 1492 (1994); (e) Folsom, H. E., Castrillon, J., Synth. Commun., 22, 1799 (1992); (f) Hirano, M., Kudo, H., Morimoto, T., Bull. Chem. Soc. Jpn., 65, 1744 (1992); (g) Hirano, M., Yakabe, S., Clark, J. H., Kudo, H., Morimoto, T., Synth. Commun., 26, 1875 (1996); (h) Ali, M. H., Stevens, W. C., Synthesis, 764 (1997); (i) Shaabani, A., Teimouri, M. B., Safaei, H. R., Synth. Commun., 30, 265 (2000); (j) Fraile, J. M., Garcia, J. I., Mayoral, J. A., Chem. Commun., 1807 (1998); (k) Firouzabadi, H., Iranpoor, N., Zolfigol, M. A., Synth. Commun., 28, 1179 (1998); (l) Firouzabadi, H., Baltork, I. M., Bull. Chem. Soc. Jpn., 65, 1131 (1992); (m) Drabowicz, J., Midura, W.,  Mikolajczyk, M., Synthesis, 39 (1979); (n) Hajipour, A. R., Baltork,  I. M., Kianfar, G., Indian J. Chem., 38B, 607 (1999); (O) Hirano, M., Yakabe, S., Itoh, S., Clark, J. H., Morimoto, T., Synthesis, 1161 (1997); (p) Hirano, M., Yakabe, S., Clark, J. H., Morimoto, T., J. Chem. Soc. Perkin Trans., 1, 2693 (1996); (q) Ali, M. H., Bohnert, G. J., Synthesis, 1238 (1988); (r) Review: Madesclaire, M., Tetrahedron, 42, 5459 (1986); (s) Review: Mata, E. G., Phosphorus, Sulfor, Silicon, 117, 1231 (1996); (t) Varma, R. S., Saini, R. K., Dahiya, R., J. Chem. Research (S), 120 (1998); (u) Varma, R. S., Saini, R. K., Meshram, H. M., Tetrahedron Lett., 38, 6525 (1997); (v)   eddy,   T. I., Varma, R. S. Chem. Commun., 471 (1997); (w) Chen, Y. J., Huang, Y. P., Tetrahedron Lett., 41, 5233 (2000); (x) Hajipour, A. R., Mallakpour, S. E., Adibi, H., J. Org. Chem.,67, 8666 (2002).
[10] Still, I. W. J., Ablenas, F. J., J. Org.  Chem., 48, 1617 (1983).
[11] Olah, G. A., Nishimura, J., J. Org.Chem., 39, 1203 (1974).
[12] Nishimura, Y., Tsuchida, E., Chem. Commun., 2099 (1996).
[13] Laali, K. K., Nagvekar, D. S., J. Org. Chem., 56, 1867 (1991).
[14] Olah,  G.  A., Marienez, E.  R., Suryaprakash, G. A., Synlett, 1397 (1999).
[15] Yadav, J.  S.,  Subba  Reddy,  B.  V.,  Rao, R. S., Pravinkumar, S., Nagaiah, K., Synlett, 784 (2002).
[16] Drabowicz.  J., Kielbasinski,  P.,  Mikolajczk,  M., ”In the chemistry of sulfones and sulfoxides”,  Patai, S., Rapopport, Z., Stirling, C. J. M., Wiley: New York,  Chapter 8 (1988).
[17] Review:  (a) Varma,  R. S.,  Green Chemistry, 43 (1999); (b) Tanaka, K., Toda, F., Chem. Rev., 100, 1025 (2000); (c) De Miguel, Y. R., Brule, E., Margue, R. G., J. Chem. Soc. Perkin Trans. 1, 3085 (2001).
[18] (a) The reaction of phenols in the presence of thionyl chloride on silica gel and FeCl3 leads to the oxidative coupling of phenols and was reduced the yields of sulfoxides intensly (Scheme 3); (b) Pines, H., Synlett, 435 (1994); (c) Toda, F., Tanaka, K., Iwata, S., J. Org. Chem., 54, 3007 (1989).
[19] (a) Shockravi, A., Rostami, E., Dehjurian, A., Tohidi, R., Tabrizi, S. B., Phosphorus, Sulfur, Silicon, 179,535 (2004); (b) Shockravi, A., Alizadeh, R., Aghabozorg, H., Moghimi, A., Rostami, E., Tabrizi, S. B., Phosphorus, Sulfur and Silicon, 178, 2519 (2003); (c) Shockravi, A., Tabrizi, S. B., Rostami, E., Yousefi, A., Dehjurian, A., Tohidi, R., J. Inclusion Phenomena, 49, 163 (2004).
Iranian Journal of Chemistry and Chemical Engineering (IJCCE)
Volume 24, Issue 3 - Serial Number 35
September and October 2005
Pages 47-52

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