Chemistry of Heterocyclic Compounds

, Volume 4, Issue 4, pp 425–426 | Cite as

Studies in the field of reactions of cyclene α-oxides

IV. Reaction of 1-methylcyclopentene oxide with alcohols
  • L. A. Mukhamedova
  • M. I. Kudryavtseva


The reaction of 1-methylcyclopentene oxide with alcohols (methanol, ethanol, n-propanol and isopropanol, n-butanol, and n-pentanol) in the presence of Na and of BF3 etherate has been described. The addition of alcohols in an alkaline medium takes place with the formation of secondary ethers of 1-methylcyclopentane-1,2-diol. In an acid medium, tertiary ethers of 1-methylcyclopentane-1,2-diol possibly contaminated with the secondary ethers are formed. In an acid medium, not only does addition take place but the initial oxide isomerizes into a carbonyl compound and to some extent forms trans-1-methylcyclopentane-1,2-diol. With isopropanol, in an alkaline medium the initial oxide is recovered and in an acid medium only the isomerization product is formed.


Oxide Alcohol Ether Methanol Carbonyl 
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  1. 1.
    L. A. Mukhamedova, T. M. Malyshko, R. R. Shagidullin, and N. V. Teptina, KhGS [Chemistry of Heterocyclic Compounds], 4, 195, 1968.Google Scholar
  2. 2.
    M. S. Malinovskii, Olefin Oxides and Their Derivatives [in Russian], Goskhimizdat, Moscow, p. 152, 1961.Google Scholar
  3. 3.
    A. Weissberger and A. Rosovsky, The Chemistry of Heterocyclic Compounds, N. Y.- London-Sydney, 1, 289, 1964.Google Scholar
  4. 4.
    A. A. Petrov, ZhOKh, 10, 981, 1940.Google Scholar
  5. 5.
    A. A. Tyazhelova, Tr. Voronezhsk. univ., 9, 140, 1957.Google Scholar
  6. 6.
    A. N. Pudovik and S. G. Denislamova, ZhOKh, 27, 2363, 1957.Google Scholar
  7. 7.
    A. A. Petrov, collection: Questions of Chemical Kinetics, Catalysis, and Reactivity [in Russian], Izdvo AN SSSR, p. 782, 1964.Google Scholar
  8. 8.
    L. A. Mukhamedova and T. M. Malyshko, Izv. AN SSSR, ser. khim., 2042, 1964.Google Scholar
  9. 9.
    J. Böeseken, Rec. trav. chim., 47, 689, 1928.Google Scholar
  10. 10.
    Chr. J. Maan, Rec. trav. chim., 48, 332, 1929.Google Scholar
  11. 11.
    G. I. Poos, G. E. Arth, R. E. Beyler, and L. H. Sarett, J. Am. Chem., Soc., 75, 422, 1953.Google Scholar
  12. 12.
    M. Goryaev and I. Pliva, Methods of Investigating Essential Oils [in Russian], Izd-vo AN Kazakhsk, SSR, Alma-Ata, p. 191, 1962.Google Scholar
  13. 13.
    Van Rysselberge, Bull. Acad. Belg., 171, 1926.Google Scholar
  14. 14.
    B. A. Arbuzov, Thesis [in Russian], Kazan, p. 209, 1936.Google Scholar
  15. 15.
    G. Chavanne and M. L. de Vogel, Bull. soc. chim., Belg., 37, 141, 1928.Google Scholar

Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • L. A. Mukhamedova
    • 1
  • M. I. Kudryavtseva
    • 1
  1. 1.Arbuzov Institute of Organic and Physical ChemistryAS USSRKazan

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