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    South African Journal of Chemistry

    On-line version ISSN 1996-840XPrint version ISSN 0379-4350

    S.Afr.j.chem. (Online) vol.63  Durban  2010

     

    RESEARCH ARTICLE

     

    Iodination of alcohols over Keggin-type heteropoly compounds: A simple, selective and expedient method for the synthesis of alkyl lodides

     

     

    Ezzat RafieeI,II, *; Houri MahdaviI; Mohammad JoshaghaniI, II

    IFaculty of Chemistry, Razi University, Kermanshah, 67149, Iran
    IIKermanshah Oil Refining Company, Kermanshah, Iran

     

     


    ABSTRACT

    Different catalysts derived from Keggin-type heteropoly compounds were prepared and their catalytic activities have been compared in the iodination of benzyl alcohol with KI under mild reaction conditions. A high catalytic activity was found over tungstophosphoric acid supported on silica and titania. The effect of catalyst loading, iodine source and the nature of substituents on the aromatic ring of benzyl alcohol were investigated. Finally, several competitive reactions were studied between structurally diverse alcohols. This protocol provides a mild and expedient way for the conversion of various alcohols to their corresponding alkyl iodides with high selectivity.

    Keywords: Keggin-type heteropoly compounds, supported catalyst, alcohols, alkyl iodides, potassium iodide


     

     

    Full text available only in PDF format.

     

    Acknowledgements

    We thank the Razi University Research Council and Kermanshah Oil Refining Company for support of this work.

     

    References

    1 M. Hudlicky and T. Hudlicky, Chemistry of Functional Groups, Wiley, New York, 1983.         [ Links ]

    2 R. Bohlmann, Comprehensive Organic Synthesis, Pergamon, Oxford, 1991.         [ Links ]

    3 B.J. Wakefield, Organolithium Methods, Academic Press, London, 1988.         [ Links ]

    4 WF. Bailey and A.D. Khanolkar, Tetrahedron, 1991, 47, 7727-7738.         [ Links ]

    5 S. Hayat, A.U. Rahman, K.M. Khan, M.I. Choudhary, G.M. Maharvi, Z. Ullah and E. Bayer, Synth. Commun., 2003, 33, 2531-2540.         [ Links ]

    6 B.P. Bandgar, VS. Sadavarte and L.S. Uppalla, Tetrahedron Lett., 2001, 42, 951-953.         [ Links ]

    7 B.P. Bandgar and S.V Bettigeri, Monatsh. Chem., 2004, 135, 1251-1255.         [ Links ]

    8 M. Di Deo, E. Marcantoni, E. Torregiani, G. Bartoli, M.C. Bellucci, M. Bosco and L. Sambri, J. Org. Chem., 2000, 65, 2830-2833.         [ Links ]

    9 M.E. Jung and P.L. Ornstein, Tetrahedron Lett., 1977, 31, 2659-2662.         [ Links ]

    10 H. Firouzabadi, N. Iranpoor and M. Jafarpour, Tetrahedron Lett., 2004, 45, 7451-7454.         [ Links ]

    11 K.M. Khan, Z. Ullah, S. Perveen, M.I. Choudhary, A.U. Rahman and W. Voelter, Lett. Org. Chem., 2005, 2, 309-311.         [ Links ]

    12 A.R. Hajipour, A. Zarei and A.E. Ruoho, Synth. Commun., 2006, 36, 1039-1050.         [ Links ]

    13 H. Tajik, F. Shirini, M.A. Zolfigol and F. Samimi, Synth. Commun., 2006, 36, 91-95.         [ Links ]

    14 A.R. Hajipour, A.R. Falahati and A.E. Ruoho, Tetrahedron Lett., 2006, 47, 4191-4196.         [ Links ]

    15 N. Iranpoor, H. Firouzabadi, Gh. Aghapour and A.R. Vaez zadeh, Tetrahedron, 2002, 58, 8689-8693.         [ Links ]

    16 B. Das, H. Holla, Y. Srinivas, N. Chowdhury and B.P. Bandgar, Tetrahedron Lett., 2007, 48, 3201-3204.         [ Links ]

    17 J.R. Satam and R.V. Jayaram, Catal. Commun., 2008, 9, 1033-1039.         [ Links ]

    18 M. Tajbakhsh, R. Hosseinzadeh and Z. Lasemi, Synlett, 2004, 635-638.         [ Links ]

    19 M.D. Bhor, A.G. Panda, N.S. Nandurkar and B.M. Bhanage, Tetrahedron Lett., 2008, 49, 6475-6479.         [ Links ]

    20 I.V. Kozhevnikov, Chem. Rev., 1998, 98, 171-198.         [ Links ]

    21 M. Misono, I. Ono, G. Koyano and A. Aoshima, Pure Appl. Chem., 2000, 72, 1305-1312.         [ Links ]

    22 M. Sadakane and E. Steckhan, Chem. Rev., 1998, 98, 219-238.         [ Links ]

    23 D. Katsoulis, Chem. Rev., 1998, 98, 359-388.         [ Links ]

    24 Y. Izumi, K. Urabe and M. Onaka, Zeolite, Clay and Heteropoly Acid in Organic Reactions, Kodansha/VCH, Tokyo, 1992.         [ Links ]

    25 I.V. Kozhevnikov, Catal. Rev. Sci. Eng., 1995, 37, 311-352.         [ Links ]

    26 L.C.W. Baker and T.P. McCutcheon, J. Am. Chem. Soc., 1956, 78, 4503.         [ Links ]

    27 L.C.W. Baker and V.E. Simmons, J. Am. Chem. Soc., 1959, 81, 4744.         [ Links ]

    28 E. Rafiee, Z. Zolfagharifar, M. Joshaghani and S. Eavani, Appl. Catal. A: Gen., 2009, 365, 287-291.         [ Links ]

    29 E. Rafiee, Sh. Tangestaninejad, M.H. Habibi and V Mirkhani, Synth. Commun., 2004, 20, 3673-3681.         [ Links ]

    30 P.J. Domaille and WH. Knoth, Inorg. Chem., 1983, 22, 818-822.         [ Links ]

    31 A.V. Golovin and K.I. Zammaraev, J. Mol. Catal. A: Chem., 1996, 114, 123-130.         [ Links ]

    30 S.P. Marsden, Contemp. Org. Synth., 1997, 4, 118-135.         [ Links ]

    32 M.N. Timofeeva, Appl. Catal. A: Gen. 2003, 256, 19-35.         [ Links ]

    33 I.A. Weinstock, Chem. Rev., 1998, 98, 113-170.         [ Links ]

     

     

    Received 10 May 2010
    Revised 24 August 2010
    Accepted 24 August 2010

     

     

    * To whom correspondence should be addressed. E-mail: ezzat_rafiee@yahoo.com / e.rafiei@razi.ac.ir