Electrophilic Aromatic Iodine Substitution of 1-[(p-Tolylimino)Methyl]-Naphthalen-2-Ol In Zeolite Catalyst

Yıl 2011, Cilt: 15 Sayı: 2, 121 - 128, 01.12.2011

Murat Gündüz Sevim Bilgiç

Öz

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Anahtar Kelimeler

Aromatic iodination, electrophilic aromatic substitution, iodoarenes, Schiff base, zeolite, catalyst

Zeolit Katalizörlüğünde 1-[(p-Tollilimino)Metil]-Naftalen-2-Ol'ün Elektrofilik Aromatik İyot Sübstitüsyonu

Öz

In this study, the naphtholic Schiff base has been reacted with iodine in the catalyst of natural zeolite clinoptilolite in order to synthesize iodine substituted Schiff base. The isolated product structure has been determined by IR, UV, 1H-NMR, 13C-NMR, Mass spectroscopy and elemental analysis. Under our reaction conditions it's found that the iodine is substituted to the phenyl ring of the naphtholic Schiff base.

Anahtar Kelimeler

Aromatik iyotlama, elektrofilik aromatik sübstitüsyon, iodoarenler, Schiff bazı, zeolit, katalizör

Kaynakça

• Merkushev, E.B., “Advances in the Synthesis of Iodoaromatic Compounds”, Synthesis, 923-925, 1988.
• Olah, G. A., Wang, Q. and Prakash, G. K., “Iodination of Deactivated Aromatics with NIodosuccinimide in Trifluoromethanesulfonic Acid via in Situ Generated Superelectrophilic Iodine(I) Trifluoromethanesulfonate”, J.Org. Chem., 58, 3194-3195, 1993.
• Wirth, H.O., Konigslen, O. and Kern, W., Liebigs Ann. Chem., 634, 84, 1960.
• Zweig, A., Huffman, K.R. and Nachtigall, G.W., “Ipso Nitration of 4-iodo-o-xylene”, J.Org. Chem., 42, 4049-4052, 1977.
• Boothe, R., Dial, C., Conaway, R., Pagni, R. M. and Kabalka, G.W., “The Iodination of Aromatic Substrates on Alumina”, Tetrahedron Lett., 27, 2207–2210, 1986.
• Blackmore, I.J., Boa, A.N., Murray, E. J., Dennis, M. and Woodward, S., A., “Simple Preparation of Iodoarenes, Iodoalkenes and Iodoalkynes by Reaction of Organolithiums with 2,2,2-trifluoro-1iodoethane”, Tetrahedron Lett., 40, 6671-6672, 1999.
• Chiappe, C. and Pieraccini, D., “Regioselective Iodination of Arenes in Ionic Liquids Mediated by SelectfluorTM Reagent F-TEDA-BF4 (MS-574HP)”, Arkivoc (xi), 249-255, 2002.
• Krishna Mohan, K.V.V., Narender, N. and Kulkarni, S.J., “Simple and Regioselective Oxyiodination of Aromatic Compounds with Ammonium Iodide and Oxone® ”, Tetrahedron Lett., 45, 8015-8016, 2004.
• Johnson, R., Meijer, A. and Ellervik, U., “Mild and Efficient Direct Aromatic Iodination”, Tetrahedron, 61, 11656-11663, 2005.
• Patil, B.R., Bhusare, R.P. and Vibhute, Y.B., “Regioselective Iodination of Hydroxylated Aromatic Ketones (06-1607JP)”, Arkivoc, (i), 104108, 2006.
• Carreno, M.C., Ruano, J.L., Sanz, G., Toledo, M.A. and Urbano, A., “Mild and Regiospecific Nuclear Iodination of Methoxybenzenes and Naphthalenes with N-iodosuccinimide in Acetonitrile”, Tetrahedron Lett., 37, 4081-4084, 1996.
• Kabalka, G.W. and Mereddy, A.R., “A Facile Synthesis of Aryl Iodides via Potassium Aryltrifluoroborates”, Tetrahedron Lett., 45, 343345, 2004.
• Harvey, R.B., Kubena, L.F. and Phillips, T.D., “Evaluation of Aluminsilicate Compounds to Reduce Aflatoxin Residues and Toxicity to Poultry and Livestock: A Review Report”, Science of the Total Environment (Suppl Pt2), 1453–1457, 1993.
• Delgado, F., Ríos, H., Aceves, J.M., Penieres, G., Arroyo, G. Velasco, B. and Miranda, R., “Characterization and Application of a New Natural Catalyst (MX-919EP)”, Arkivoc (xi), 118131, 2003.
• Jansen, J.C., Karge, H.G. and Weitkamp, J., “Advanced Zeolite Science and Application; Studies in Surface Science and Catalysis”, Vol. 85, Elsevier, Amsterdam, 1994.
• Reddy, K.S.N., Rao, B.S. and Shiralkar, V.P., “Reforming of Pyrolysis Gasoline over Platinumalumina Catalysts Containing MFI type Zeolites”, Appl. Catal., 95, 53-63, 1993.
• Pradhan, A.R. and Rao, B.S., “Transalkylation of di-isopropylbenzenes over Large Pore Zeolites”, Appl. Catal., 106, 143-153, 1993.
• Weigert, F.J., U.S. Patent 4,593,124, 1986.
• Singh, A.P. and Kale, S.M., U.S. Patent 5,892,138, 1999.
• Singh, A.P., Bandyopadhyay, R. and Rao, B.S., “Vapour Phase Beckmann Rearrangement of Cyclohexanone Oxime over SAPO-11 Molecular Sieve”, Appl. Catal., 136, 249-263, 1996.
• Thangaaraj, A., Sivasanker S. and Ratnasamy, P., “Zeolites”, 135, 1992.
• Iwamoto, M., Yashiro, H., Tandaa, K. and Mizumo, N., J. Phys. Chem., 95, 3727-3729, 1991.
• Tobias, M.A., U.S. Patent 3,728,408, 1973.
• Venkateshan, C., Jaimol, T., Moreau, P., Finiels, A., Ramaswamy, A.V. and Singh, A.P., “Liquid Phase Selective Benzoylation of Chlorobenzene to 4,4 -Dichlorobenzophenone over Zeolite H-Beta”, Catal. Lett., 75, 119-123, 2001.
• Ratnasamy, P., Singh, A.P. and Sharma, S., “Halogenation over Zeolite Catalysts”, Appl. Catal. A, 135, 25-55, 1996.
• Arisawa, M., Suwa, A., Ashikawa, M. and Yamaguchi, M., “One-pot Aromatic Brominationrearrangement Catalyzed by GaCl3 (KF-730HP)”, Arkivoc (viii), 24-34, 2003.
• Kale, S.M., “Halogenation and Isomerization Reactions of Aromatics over K-L, H-beta and HZSM-5 Zeolite Catalysts”, Ph.D. thesis, Catalysis Division National Chemical Laboratory, University of Pune, India, 2002.
• Sawich, A. and Zetensow, J.V., Astron. Fiz. Khim. Spit Syn, I., 1, 233, 1956.
• Linares, C.F., Goldwasser, M.R., Machado, F.J., Rivera, A., Rodriguez-Fuentes, G. and Barrault, J., “Advantages of Base Exchanged Natural Clinoptilolite as a Catalyst for the Knoevenagel Reaction”, Microporous Mesoporous Mater., 41, 69-77, 2000.
• Gündüz, M. and Bilgiç, S., “1-(N-para-iyodoorto-metilfeniliminometil)-2-naftol’ün Sentezi”, Anadolu University Journal of Science and Technology, 8(2), 159-165, 2007.
• Gündüz, M. and Bilgiç, S., Bilgiç O., Özöğüt, D., “Novel Electrophilic Aromatic Iodine Substitution of Some Naphtholic Schiff Bases”, Arkivoc (xiii), 115-121, 2008.