Shockravi,, A., Rostami, E., Zakeri, M. (2005). A Solvent Free Route to the Synthesis of Diaryl Sulfoxides. Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 24(3), 47-52.
Abbas Shockravi,; Esmael Rostami; Masoomeh Zakeri. "A Solvent Free Route to the Synthesis of Diaryl Sulfoxides". Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 24, 3, 2005, 47-52.
Shockravi,, A., Rostami, E., Zakeri, M. (2005). 'A Solvent Free Route to the Synthesis of Diaryl Sulfoxides', Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 24(3), pp. 47-52.
Shockravi,, A., Rostami, E., Zakeri, M. A Solvent Free Route to the Synthesis of Diaryl Sulfoxides. Iranian Journal of Chemistry and Chemical Engineering (IJCCE), 2005; 24(3): 47-52.
A Solvent Free Route to the Synthesis of Diaryl Sulfoxides
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.
[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. PerkinTrans.,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 andSilicon, 178, 2519 (2003); (c) Shockravi, A., Tabrizi, S. B., Rostami, E., Yousefi, A., Dehjurian, A., Tohidi, R., J. InclusionPhenomena, 49, 163 (2004).
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