Russian Chemical Bulletin

, Volume 48, Issue 12, pp 2279–2284 | Cite as

Unusually facile transformations of cyclopentane into cyclohexanes, decalins, and adamantanes

  • I. S. Akhrem
  • S. V. Vitt
  • I. M. Churilova
  • A. V. Orlinkov
Organic Chemistry


Cyclopentane is converted into a mixture of cyclohexanes, decalins, and adamantanes (and isomeric cycloalkanes) in overall yields of 18–31% (w/w) under the action of superelectrophilic complex CBr4·2AlBr3 either in CH2X2 (X=Br, Cl) or without a solvent at 20°C.

Key words

cyclopentane cyclohexanes decalins adamantanes tricyclanes superelectrophilic complex CBr4·2AlBr3 cyclooligomerization GLC-MS analysis 


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  1. 1.
    I. Akhrem, A. Orlinkov, and M. Vol'pin,J. Chem. Soc., Chem. Commun., 1993, 671.Google Scholar
  2. 2.
    I. S. Akhrem and A. V. Orlinkov,Izv. Akad. Nauk, Ser. Khim., 1998, 771 (and references therein) [Russ. Chem. Bull., 1998,47, 740 (Engl. Transl.)].Google Scholar
  3. 3.(a)
    J. H. Beynon,Mass Spectrometry and its Applications to Organic Chemistry, Elsevier, Amsterdam, 1960; (b) F. W. Lafferty,Mass Spectrometry of Organic Ions, Academic Press, New York, 1963; (c) A. A. Polyakova and R. A. Khmel'nitskii,Mass-spektrometriya v organicheskoi khimii [Mass Spectrometry in Organic Chemistry], Khimiya, Moscow, 1972 (in Russian); (d) A. A. Polykova, E. V. Khramova, E. I. Bagrii, N. N. Tsitsugina, I. M. Lukashenko, and T. Yu. Frid,Neftekhimiya [Petrochemistry], 1973,13, 9 (in Russian); (e) L. Doleysek, S. Hala, V. Hames, and S. Landa,Collection, 1966,31, 435; (f) E. S. Brodskii, I. M. Lukashenko, I. A. Musaev, E. Kh. Kurashova, and P. I. Sanin,Neftekhimiya [Petrochemistry], 1976,16, 13 (in Russian).Google Scholar
  4. 4.
    G. N. Gordadze, I. A. Matveeva, M. N. Zabrodina, and G. N. Rusinova,Neftekhimiya [Petrochemistry], 1998,38, 42 (in Russian).Google Scholar
  5. 5.(a)
    E. I. Bagrii, inAdamantany, poluchenie, svoistva, primenenie [Adamantanes, Preparation, Properties, Application], Nauka, Moscow, 1989, p. 70; (b) P. R. Schleyer, G. J. Gleicher, and C. A. Cupas,J. Org. Chem., 1966,31, 2014.Google Scholar
  6. 6.
    B. G. Gavrilov, V. G. Luksha, and S. F. Aver'yanov,Zh. Prikl. Khim., 1978,51, 671 [J. Appl. Chem. USSR, 1978,51 (Engl. Transl.)].Google Scholar
  7. 7.
    B. G. Gavrilov, V. G. Luksha, and L. N. Tropinova,Zh. Org. Khim., 1976,12, 1599 [J. Org. Chem. USSR, 1976,12 (Engl. Transl.)].Google Scholar
  8. 8.
    J. T. Eidus,Z. Org. Chem. 1968,4, 1214.Google Scholar
  9. 9.(a)
    H. Koch and W. Haaf,Liebigs Ann. Chem., 1958,618, 251; (b) H. Bahrmann, inNew Syntheses with Carbon Monoxide, Ed. J. Falbe, Springer-Verlag, Berlin, 1980, 372.Google Scholar
  10. 10.
    G. Olah and J. Lukas,J. Am. Chem. Soc., 1968,90, 933.CrossRefGoogle Scholar

Copyright information

© Kluwer Academic/Plenum Publishers 2000

Authors and Affiliations

  • I. S. Akhrem
    • 1
  • S. V. Vitt
    • 1
  • I. M. Churilova
    • 1
  • A. V. Orlinkov
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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