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Chemical Papers

, 62:329 | Cite as

Synthesis of 2-methyl-2-propoxypropyl isocyanide and its Cu(I) tetraflouroborate complex

  • Mahmoud M. Al-KtaifaniEmail author
  • Adnan A. Nakawa
  • Zouheir A. Tabbaa
  • Adel A. Namou
Short Communication
  • 53 Downloads

Abstract

2-Methyl-2-propoxypropyl isocyanide [CNCH2C(OPr)(CH3)2] and its Cu(I) tetrafluoroborate complex [Cu{CNCH2C(OPr)(CH3)2}4]BF4 were prepared in good yields and purities. Both compounds were fully characterized by IR and NMR spectroscopy.

Keywords

isocyanide Cu(I) tetrafluoroborate complex propoxy IR NMR 

References

  1. Barybin, M. V., Young, V. G., & Ellis, J. E. (2000). First paramagnetic zerovalent transition metal isocyanides. Syntheses, structural characterizations and magnetic properties of novel low-valent isocyanide complexes of vanadium. Journal of the American Chemical Society, 122, 4678–4691. DOI: 10.1021/ja000212w.CrossRefGoogle Scholar
  2. Caro, C. F., Hitchcock, P. B., Lappert, M. F., & Layh, M. (1998). Neutral isonitrile adducts of alkali and alkaline earth metals. Chemical Communications, 1998, 1297–1298. DOI: 10.1039/a708976g.CrossRefGoogle Scholar
  3. Deicas, B., Gambino, D., Kremer, C., Kremer, E., Mombrú, A., Suescun, L., Mariezcrrena, R., González, O., Rey, A., Mallo, L., & León, A. (1997). Synthesis, characterization and cpectroscopic properties of [CuI(alkylisocyanide)4]BF4 complexes. X-ray crystal structures of [Cu(MIBI)4]BF4 and [Cu(CPI)4]BF4. Polyhedron, 16, 2397–2403. DOI: 10.1016/S0277-5387(96)00566-9.CrossRefGoogle Scholar
  4. Dönnecke, D., & Imhof, W. (2003). The formation of cis-and trans-[Ru(CN)2(CNtBu)4] by reductive cleavage of isocyanide ligands; isomer separation by supramolecular interactions with various solvents. Journal of the Chemical Society Dalton Transactions, 2003, 2737–2744. DOI: 10.1039/b304199a.Google Scholar
  5. Elschenbroich, Ch., & Salzer, A. (1992). Organometallics: A concise introduction (2nd revised ed.). Weinheim: VCH.Google Scholar
  6. Henderson, J. I., Feng, S., Bein, T., & Kubiak, C. P., (2000). Adsorption of diisocyanides on gold. Langmuir, 16, 6183–6187. DOI: 10.1021/1a9906323.CrossRefGoogle Scholar
  7. Jacox, M. E. (1994). Vibrational and electronic energy levels of polyatomic transient molecules. In J. W. Gallagher (Ed.), Journal of physical and chemical reference data, Monograph No. 3 (pp. 1–461). Washington, DC: American Chemical Society.Google Scholar
  8. Kemp, W. (1991). Organic spectroscopy (3rd ed.). London: W. H. Freeman & Company.Google Scholar
  9. Leach, P. A., Geib, S. J., Corella II, J. A., Warnock G. F., & Cooper, N. J. (1994). Synthesis and structural characterization of [Co{CN(2,6-C6H3Me2)}4], the first transition metal isonitrilate. Journal of the American Chemical Society, 116, 8566–8574. DOI: 10.1021/ja00098a017.CrossRefGoogle Scholar
  10. Lee, T.-W., Su, C.-S., & Ting, G. (1996). Synthesis, reactivity and 99mTc labelling of 2-alkoxyisobutylisonitrile. Applied Radiation and Isotopes, 47, 207–210. DOI: 10.1016/0969-8043(95)00249-9.CrossRefGoogle Scholar
  11. Mathieson, T., Schier, A., & Schmidbaur, H. (2001). Supramolecular chemistry of gold(I) thiocyanate complexes with thiophene, phosphine and isocyanide ligands, and the structure of 2,6-dimethylphenyl isocyanide. Journal of Chemical Society, Dalton Transactions, 2001, 1196–1200. DOI: 10.1039/b100117p.CrossRefGoogle Scholar
  12. Moigno, D., Callejas-Gaspar, B., Gil-Rubio, J., Brandt, C. D., Werner, H., & Kiefer, W. (2002). Preparation, molecular structure, and fundamental vibrational modes of the dinuclear complexes trans-[{RhX(PiPr3)2}2 ??{μ-1,3-(CN)2C6H4}]. Inorganica Chimica Acta, 334, 355–364. DOI: 10.1016/S0020-1693(02)00801-0.CrossRefGoogle Scholar
  13. Perrin, D. D., & Armarego, W. L. F. (1988). Purification of laboratory chemicals (3rd ed.). Oxford: Butterworth-Heinemann, Ltd.Google Scholar
  14. Porcheddu, A., Giacomelli, G., & Salaris, M. (2005). Microwave-assisted synthesis of isonitriles: A general simple methodology. Journal of Organic Chemistry, 70, 2361–2363. DOI: 10.1021/jo047924f.CrossRefGoogle Scholar
  15. Rasika Dias, H. V., & Jin, W. (1995). Chemistry of trifluoromethylated tris(pyrazolyl)borate: Synthesis and characterization of carbonyl and isonitrile adducts of silver(I). Journal of American Chemical Society, 117, 11381–11382. DOI: 10.1021/ja00150a053.CrossRefGoogle Scholar
  16. Sugihara, T., Yamada, M., & Nishizawa, M. (1998). Synthesis of isonitrile complexes of group-VI metal carbonyls and their use as mediator in the [2+2+2]-cyclization of alkynes. Journal of the Indian Chemical Society, 75, 645–647.Google Scholar
  17. Treichel, P. M. (1973). Transition metal-isocyanide complexes. Advances in Organometallic Chemistry, 11, 21–85.CrossRefGoogle Scholar
  18. Ugi, I., Fetzer, U., Eholzer, U., Knupfer, H., & Offermann, K. (1965). Isonitrile syntheses. Angewandte Chemie International Edition in English, 4, 472–484. DOI: 10.1002/anie.196504721.CrossRefGoogle Scholar
  19. Utz, T. L., Leach, P. A., Ceib, S. J., & Cooper, N. J. (1997). Synthesis, derivatization, and structural characterization of [Mn(CNC6H3Me2-2,6)5], a five-coordinate isonitrilate complex containing Mn−1. Chemical Cummunications, 1997, 847–848. DOI: 10.1039/a700089h.CrossRefGoogle Scholar
  20. Van Wyk, A. J., Van Aswegen, A., Knoesen, O., Fourie, P. J., Koekemoer, J., Herbst, C. P., Otto A. C., & Lötter, M. G. (1991). Synthesis and 99mTc labelling of MMI (MIBI) and its ethyl analogue EMI. International Journal of Radiation Applications and Instrumentation. Part A. Applied Radiation and Isotopes, 42, 687–689. DOI: 10.1016/0883-2889(91)90041-X.CrossRefGoogle Scholar
  21. Weber, W. P., & Gokel, G. W. (1972). An improved procedure for the Hofmann carbylamine synthesis of isonitriles. Tetrahedron Letters, 13, 1637–1640. DOI: 10.1016/S0040-4039(01)84707-9.CrossRefGoogle Scholar

Copyright information

© Versita 2008

Authors and Affiliations

  • Mahmoud M. Al-Ktaifani
    • 1
    Email author
  • Adnan A. Nakawa
    • 1
  • Zouheir A. Tabbaa
    • 1
  • Adel A. Namou
    • 1
  1. 1.Department of ChemistryAtomic Energy CommissionDamascusSyria

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