ELECTROPHILIC AROMATIC IODINE SUBSTITUTION OF 1-{[(PHENYL)IMINO]METHYL}NAPHTHALEN-2-OL1

Yıl 2008, Sayı: 017, 53 - 60, 15.12.2008

Murat Gündüz

Öz

In this paper, a simple, direct and environment friendly procedure for the iodination of naphtholic Schiff base is

presented. Naphtholic Schiff base was regioselectively iodinated in the presence of zeolite under mild conditions.

The procedure has been extended to the iodination of other aromatic and hetero aromatic compounds.

Anahtar Kelimeler

Aromatic iodination, iodoarenes, Schiff base, zeolite

1-{[(FENİL)İMİNO]METİL}NAFTALEN-2-OL’ÜN ELEKTROFİLİK AROMATİK İYOT SÜBSTİTÜSYONU

Öz

Bu makalede, Naftolik Schiff bazının iyotlanması için basit, direkt ve çevre dostu bir yöntem sunulmuştur.

Naftolik Schiff bazı, zeolit varlığında, ılımlı koşullar altında seçici olarak iyotlanmıştır. Bu yöntem diğer

aromatik ve hetero aromatik bileşiklerinin iyotlanmasında da uygulanabilir.

Anahtar Kelimeler

Aromatik iyotlama, iodoarenler, Schiff bazı, zeolit, katalizör

Kaynakça

• [1] Fanta, P.E., “The Ullmann synthesis of biaryls”, Synthesis, 9-21 (1974).
• [2] Diederich, F. and Stang, P.J., “Metal-Catalyzed Cross-Coupling Reactions”, Wiley-VCH: Weinheim,Germany, 358-372 (1998).
• [3] Skulski, L., “Organic iodine ( I, III, V ) chemistry: 10 years of development at the Medical University of Warsaw, Poland (1990-2000)”, Molecules, 5: 1331-1371 (2000).
• [4] Merkushev, E.B., “Advances in the synthesis of iodoaromatic compounds”, Synthesis, 923 (1988).
• [5] Chiappe, C. and Pieraccini, D., “Regioselective iodination of arenes in ionic liquids mediated by selectfluorTM reagent F-TEDA-BF4”, Arkivoc, xi: 249-255 (2002).
• [6] Colella, C., “Ion exchange equilibria in zeolite materials”, Mineralium Deposita, 31 (6): 554–562 (1996).
• [7] Mumpton, F.A., Proc. Natl. Acad. Sci., 96: 3463 (1999).
• [8] Dyer, A., “An Introduction to Zeolite Molecular Sieves”, Wiley & Sons, Chichester, 88-92 (1988).
• [9] Jansen, J.C., Karge, H.G., Weitkamp, J., Advanced Zeolite Science and Application; Studies in Surface Science and Catalysis, Elsevier, Amsterdam, 85: 244-256, (1994).
• [10] Reddy, K.S.N., Rao, B.S. and Shiralkar, V.P., “Reforming of pyrolysis gasoline over platinum-alumina catalysts containing MFI type zeolites”, Appl. Catal., 95: 53-63 (1993).
• [11] Pradhan, A.R. and Rao, B.S., “Transalkylation of di-isopropylbenzenes over large pore zeolites”, Appl.Catal., 106: 143-153 (1993).
• [12] Weigert, F.J., U.S. Patent, 4,593,124 (1986).
• [13] Singh, A.P. and Kale, S.M., U.S. Patent, 5,892,138 (1999).
• [14] 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).
• [15] Thangaraj, A., Sivasanker S. and Ratnasamy, P., “Evidence for the simultaneous incorporation of Al and Ti in MFI structure (Al-TS-1)”, Zeolites, 135-137 (1992).
• [16] Iwamoto, M., Yashiro, H., Tandaa, K. and Mizumo, N., “Removal of nitrogen monoxide through a novel catalytic process”, J. Phys. Chem., 95(9): 3727-3730 (1991).
• [17] Tobias, M.A., U.S. Patent, 3,728,408 (1973).
• [18] 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). D.P.Ü. Fen Bilimleri Enstitüsü Electrophilic Aromatic Lodine Substitution of 17. Sayı Aralık 2008 1{[(Phenyl)Imino]Methyl}Naphthalen-2-OL1 M.GÜNDÜZ & S.BİLGİÇ 60
• [19] Ratnasamy, P., Singh, A.P. and Sharma, S., “Halogenation over zeolite catalysts”, Appl. Catal. A, 135: 25-55 (1996).
• [20] Roy, S.C., Rana, K.K., Guin, C. and Banerjee, B., “Ceric ammonium nitrate catalyzed mild and efficient α-chlorination of ketones by acetyl chloride”, Arkivoc, ix: 34-38 (2003).
• [21] Gnaim, J.M. and Sheldon, R.A., “Regioselective bromination of aromatic compounds with Br2/SO2Cl2 over microporous catalysts”, Tetrahedron Lett., 46: 4465-4468 (2005).
• [22] Csunderlik, C., Bercean, V., Peter, F. and Badea, V., “Facile bromination of the benzene ring during the cyclisation of the 1H-3-methyl-4-ethoxycarbonyl-5-arylidenehydrazonopyrazoles to the 3- substituted-aryl-1H-6-methyl-7-ethoxycarbonyl-pyrazolo[3,2-c]-s-triazoles”, Arkivoc, ii: 133-141 (2002).
• [23] Kale, S.M., “Halogenation and Isomerization Reactions of Aromatics over K-L, H-beta and H-ZSM-5 Zeolite Catalysts”, Ph.D. Thesis, Catal. Div. Nat. Chem. Lab., University of Pune, India. (2002).
• [24] Szostak, R., “Handbook of Molecular Sieves”, Springer, New York, 342-356 (1982).
• [25] Tihmillioglu, F. and Ulku, S., “Use of clinoptilolite in ethanol dehydration”, Sep. Sci. Tech., 31: 2855-2865 (1996).
• [26] 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).
• [27] Gündüz, M. and Bilgiç, S., “1-(N-para-iyodo-orto-metilfeniliminometil)-2-naftol’ün sentezi”, Anadolu Üniversitesi Bilim ve Teknoloji Dergisi, 8(2): 159-165, (2007).
• [28] Sawich, A. and Zetensow, J.V., Astron. Fiz. Khim. Spit Syn, I., 1: 233-242 (1956).
• [29] Young, L.B., Butter, S.A., Kaeding, W. and Young, W., “Shape selective reactions with zeolite catalysts III. Selectivity in xylene isomerization, toluene-methanol alkylation, and toluene disproportionation over ZSM-5 zeolite catalysts “, J. Catal. 1982, 76: 418-432 (1982).
• [30] Miyake, K., Sekizawa, K., Hironaka, T., Nakano, M., Fujii, S. and Tsutsumi, Y., “Selective parabromination of phenyl acetate under the control of zeolites, bases, acetic anhydride or metal acetates in the liquid phase“ Stud. Surf. Sci. Catal., 28: 747-758 (1986).
• [31] Ratnamasy, P., Singh, A.P. and Sharma, S., “Halogenation over zeolite catalysts” Applied Catalysis A,135: 25-55 (1996).