How to cite this paper
Damghani, K., Pourmousavi, S & Fahid, F. (2014). Regioselective nitration of phenols using Sr(NO3)2 or benzyltriphenylphosphonium nitrate in the presence of H2SO4-silica under solvent free conditions.Current Chemistry Letters, 3(4), 207-214.
Refrences
1 Vogel A. A. (1978) Text Book of Practical Organic Chemistry, 4th Ed, Longman, London, 937-940.
2 Ouertani M., Giraro P., and Kagan H. B. (1982) Selective nitration of phenols catalyzed by lanthanum (III) nitrate. Tetrahedron Lett., 23, 4315-4318.
3 Gigante B., Prazeres A. O., Marcelo-Curto M. J., Cornelis A., and Laszlo P. (1995) Mild and Selective Nitration by Claycop. J. Org. Chem. 60, 3445-4347.
4 Pervez H., Onyiriuka S. O., Rees L., Rooney J. R., and Suckling C. J. (1988) Selective functionalisatlon: Part 10. The nitration of phenols by pyridine derivatives carrying a transferable nitro group. Tetrahedron, 44, 4555- 4565.
5 Dagade S. P., Kadam V. S., and Dongare M. K. (2002) Regioselective nitration of phenol over solid acid catalysts. Catal. Commun., 3, 67- 70.
6 Beheshti S., Kianmehr E., Yahyaee M., and Tabatabai K. (2006) Facile and Efficient Selective Mono-nitration of Phenols under Solvent-free Conditions. Bull. Korean Chem. Soc., 27, 1056- 1058.
7 Smith K., Musson A., and DeBoss G. A. (1996) Superior methodology for the nitration of simple aromatic compounds. Chem. Commun., 469-470.
8 Yadav G. D., and Nair J. J. (1999) Selectivity engineering in the nitration of chlorobenzene using eclectically engineered sulfated zirconia and carbon molecular sieve catalysts. Catal. Lett., 62, 49-52.
9 Sana S., Rajanna K. C., Ali M. M., and Saiprakash P. K. (2000) Mild, efficient and selective nitration of anilides, non-activated and moderately activated aromatic compounds with ammonium molybdate and nitric acid as a new nitrating agent. Chem. Lett. 48-49.
10 Choudary B. M., Sateesh M., Kantam M. L., Rao K. K., Prasad K. V. R., Raghavan K. V., and Sarma J. A. R. P. (2000) Chem. Commun. 25–26.
11 Rodrigues J. A. R., de Oliveira Fillho A. P., Moran P. J. S., and Custodio R. (1999) Regioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gel. Tetrahedron, 55, 6733-6738.
12 Milczak T., Jacniacki J., Zawadzki J., Malesa M., and Skupi?ski W. (2001) Nitration of aromatic compounds on solid catalysts. Synth. Commun., 31, 173-187.
13 Loupy A., Maurel F., and Sabatie-Gogova A. (2004) Improvements in Diels–Alder cycloadditions with some acetylenic compounds under solvent-free microwave-assisted conditions: experimental results and theoretical approaches. Tetrahedron, 60, 1683-1691.
14 Pchelka B K., Loupy A., and Petit A. (2006) Improvement and simplification of synthesis of 3-aryloxy-1,2-epoxypropanes using solvent-free conditions and microwave irradiations. Relation with medium effects and reaction mechanism. Tetrahedron, 62, 10968-10979.
15 Varma R. S., Chatterjee A. K., and Varma M. (1993) Alumina-mediated deacetylation of benzaldehyde diacetates. A simple deprotection method. Tetrahedron Lett., 34, 3207-3210.
16 Kumar D., Sundaree M. S., Patel G., Rao V. S., and Varma R. S. (2006) Solvent-free facile synthesis of novel ?-tosyloxy B-keto sulfones using [hydroxy(tosyloxy)iodo]benzene. Tetrahedron Lett., 47, 8239-8241.
17 Hajipour A. R., Zarei A., and Ruoho A. E. (2007) P2O5/Al2O3 as an efficient heterogeneous catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions. Tetrahedron Lett., 48, 2881-2884.
18 Hajipour A. R., and Ruoho A. E. (2004) A fast and mild method for nitration of aromatic ring. Phosphorus, Sulfur Silicon Relat. Elem., 179, 221-226.
19 Baghernejad B., Heravi M. M., Oskooie H. A., and Beheshtiha Y. S. (2009) An efficient and regioselective nitration of phenols using NH4NO3, KHSO4. G.U. Journal of Science, 22, 169-173.
20 Anuradha V., Srinivas P. V., Aparna P., and Madhusudana Rao J. (2006) p-Toluenesulfonic acid catalyzed regiospecific nitration of phenols with metal nitrates. Tetrahedron Lett., 47, 4933-4935.
21 Crivello J. V. (1981) Nitrations and oxidations with inorganic nitrate salts in trifluoroacetic anhydride. J. Org. Chem., 46, 3056-3060.
22 Zolfigol M. A., Madrakian E., and Ghaemi E. (2002) Silica sulfuric acid/NaNO2 as a novel heterogeneous system for the nitration of phenols under mild conditions. Molecules, 7, 734-742.
23 Hajipour A. R., Zarei A., and Ruoho A. E. (2005) Supported bismuth(III) nitrate on silica sulfuric acid as useful reagent for nitration of aromatic compounds under solvent-free conditions. Russ. J. Org. Chem., 41, 1493-1495.
24 Sun H. B., Hua R., and Yin Y. (2005) Highly efficient nitration of phenolic compounds in solid phase or solution using Bi(NO3)3•5H2O as nitrating reagent. J. Org. Chem., 70, 9071-9073.
25 Muathen H. A. (2003) Selective Nitration of Aromatic Compounds with Bismuth Subnitrate and Thionyl Chloride. Molecules, 8, 593-598.
26 Yadav U., Mande H., and Ghalsasi P. (2012) Nitration of Phenols Using Cu(NO3)2: Green Chemistry Laboratory Experiment. J. Chem. Educ., 89, 268?270.
27 Gaude D., Le Goaller R., and and Pierre J. L. (1986) Nitration of Phenols with Nitrates in a Two-Phase System. Synth. Commun., 16, 63-68.
28 (1982) Dictionary of Organic Compounds, 5th Ed, Chapman and Hall.
29 Pourmousavi S. A., and Zinati Z. (2009) H2SO4-silica as an efficient and chemoselective catalyst for the synthesis of acylal from aldehydes under solvent-free conditions. Turk. J. Chem., 33, 385-392.
2 Ouertani M., Giraro P., and Kagan H. B. (1982) Selective nitration of phenols catalyzed by lanthanum (III) nitrate. Tetrahedron Lett., 23, 4315-4318.
3 Gigante B., Prazeres A. O., Marcelo-Curto M. J., Cornelis A., and Laszlo P. (1995) Mild and Selective Nitration by Claycop. J. Org. Chem. 60, 3445-4347.
4 Pervez H., Onyiriuka S. O., Rees L., Rooney J. R., and Suckling C. J. (1988) Selective functionalisatlon: Part 10. The nitration of phenols by pyridine derivatives carrying a transferable nitro group. Tetrahedron, 44, 4555- 4565.
5 Dagade S. P., Kadam V. S., and Dongare M. K. (2002) Regioselective nitration of phenol over solid acid catalysts. Catal. Commun., 3, 67- 70.
6 Beheshti S., Kianmehr E., Yahyaee M., and Tabatabai K. (2006) Facile and Efficient Selective Mono-nitration of Phenols under Solvent-free Conditions. Bull. Korean Chem. Soc., 27, 1056- 1058.
7 Smith K., Musson A., and DeBoss G. A. (1996) Superior methodology for the nitration of simple aromatic compounds. Chem. Commun., 469-470.
8 Yadav G. D., and Nair J. J. (1999) Selectivity engineering in the nitration of chlorobenzene using eclectically engineered sulfated zirconia and carbon molecular sieve catalysts. Catal. Lett., 62, 49-52.
9 Sana S., Rajanna K. C., Ali M. M., and Saiprakash P. K. (2000) Mild, efficient and selective nitration of anilides, non-activated and moderately activated aromatic compounds with ammonium molybdate and nitric acid as a new nitrating agent. Chem. Lett. 48-49.
10 Choudary B. M., Sateesh M., Kantam M. L., Rao K. K., Prasad K. V. R., Raghavan K. V., and Sarma J. A. R. P. (2000) Chem. Commun. 25–26.
11 Rodrigues J. A. R., de Oliveira Fillho A. P., Moran P. J. S., and Custodio R. (1999) Regioselectivity of the nitration of phenol by acetyl nitrate adsorbed on silica gel. Tetrahedron, 55, 6733-6738.
12 Milczak T., Jacniacki J., Zawadzki J., Malesa M., and Skupi?ski W. (2001) Nitration of aromatic compounds on solid catalysts. Synth. Commun., 31, 173-187.
13 Loupy A., Maurel F., and Sabatie-Gogova A. (2004) Improvements in Diels–Alder cycloadditions with some acetylenic compounds under solvent-free microwave-assisted conditions: experimental results and theoretical approaches. Tetrahedron, 60, 1683-1691.
14 Pchelka B K., Loupy A., and Petit A. (2006) Improvement and simplification of synthesis of 3-aryloxy-1,2-epoxypropanes using solvent-free conditions and microwave irradiations. Relation with medium effects and reaction mechanism. Tetrahedron, 62, 10968-10979.
15 Varma R. S., Chatterjee A. K., and Varma M. (1993) Alumina-mediated deacetylation of benzaldehyde diacetates. A simple deprotection method. Tetrahedron Lett., 34, 3207-3210.
16 Kumar D., Sundaree M. S., Patel G., Rao V. S., and Varma R. S. (2006) Solvent-free facile synthesis of novel ?-tosyloxy B-keto sulfones using [hydroxy(tosyloxy)iodo]benzene. Tetrahedron Lett., 47, 8239-8241.
17 Hajipour A. R., Zarei A., and Ruoho A. E. (2007) P2O5/Al2O3 as an efficient heterogeneous catalyst for chemoselective synthesis of 1,1-diacetates under solvent-free conditions. Tetrahedron Lett., 48, 2881-2884.
18 Hajipour A. R., and Ruoho A. E. (2004) A fast and mild method for nitration of aromatic ring. Phosphorus, Sulfur Silicon Relat. Elem., 179, 221-226.
19 Baghernejad B., Heravi M. M., Oskooie H. A., and Beheshtiha Y. S. (2009) An efficient and regioselective nitration of phenols using NH4NO3, KHSO4. G.U. Journal of Science, 22, 169-173.
20 Anuradha V., Srinivas P. V., Aparna P., and Madhusudana Rao J. (2006) p-Toluenesulfonic acid catalyzed regiospecific nitration of phenols with metal nitrates. Tetrahedron Lett., 47, 4933-4935.
21 Crivello J. V. (1981) Nitrations and oxidations with inorganic nitrate salts in trifluoroacetic anhydride. J. Org. Chem., 46, 3056-3060.
22 Zolfigol M. A., Madrakian E., and Ghaemi E. (2002) Silica sulfuric acid/NaNO2 as a novel heterogeneous system for the nitration of phenols under mild conditions. Molecules, 7, 734-742.
23 Hajipour A. R., Zarei A., and Ruoho A. E. (2005) Supported bismuth(III) nitrate on silica sulfuric acid as useful reagent for nitration of aromatic compounds under solvent-free conditions. Russ. J. Org. Chem., 41, 1493-1495.
24 Sun H. B., Hua R., and Yin Y. (2005) Highly efficient nitration of phenolic compounds in solid phase or solution using Bi(NO3)3•5H2O as nitrating reagent. J. Org. Chem., 70, 9071-9073.
25 Muathen H. A. (2003) Selective Nitration of Aromatic Compounds with Bismuth Subnitrate and Thionyl Chloride. Molecules, 8, 593-598.
26 Yadav U., Mande H., and Ghalsasi P. (2012) Nitration of Phenols Using Cu(NO3)2: Green Chemistry Laboratory Experiment. J. Chem. Educ., 89, 268?270.
27 Gaude D., Le Goaller R., and and Pierre J. L. (1986) Nitration of Phenols with Nitrates in a Two-Phase System. Synth. Commun., 16, 63-68.
28 (1982) Dictionary of Organic Compounds, 5th Ed, Chapman and Hall.
29 Pourmousavi S. A., and Zinati Z. (2009) H2SO4-silica as an efficient and chemoselective catalyst for the synthesis of acylal from aldehydes under solvent-free conditions. Turk. J. Chem., 33, 385-392.