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

Abstract

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 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  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

Personalised recommendations