Skip to main content
SpringerLink
Log in

Investigation of the stepwise mechanism of the acid-catalyzed condensation of 3-methyl-3-buten-1-ol with formaldehyde

  • Physical Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The primary product of condensation of 3-methyl-3-buten-1-ol with formaldehyde is 3-methyl-1,3,5-pentanetriol, while 4-methyl-4-hydroxyethyl-1,3-dioxane is formed as a result of a secondary reaction of acetalization of the triol.

  2. 2.

    The selectivity of the process with at respect to the formation of a triol or dioxane depends on the concentration of formaldehyde and the alkenol, the temperature and duration of the reaction.

  3. 3.

    The kinetic principles established for the reactions studied agree with the carbonium ion mechanism of the process.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. J. H. Prins, Recueil Trav. Chim.,51, 469 (1932); J. H. Prins, Recueil Trav. Chim.,72, 867 (1953); V. I. Isagulyants, T. G. Khaimova, V. R. Melikyan, and S. V. Pokrovskaya, Usp. Khimii,37, 61 (1968); I. Ap'ok, M. Bartok, R. A. Karakhanov, and N. I. Shuikin, Usp. Khimii, 38, 72 (1969).

    Google Scholar 

  2. C. Price, Mechanisms of Reactions at Carbon-Carbon Double Bonds, Inter. Publish., New York (1946), p. 45.

    Google Scholar 

  3. E. Érendeil and L. Mikeshka, Usp. Khimii,23, 223 (1954).

    Google Scholar 

  4. V. Franzen and H. Krauch, Chemiker-Ztg.,79, 335 (1955); J. Herscovici, M. Duvalma, A. Brenman, and R. Stoika, Rev. Chim.,14, 447 (1963).

    Google Scholar 

  5. M. I. Farberov, Ya. I. Rotshtein, A. M. Kut'in, and N. K. Shemyakina, Zh. Obshch. Khimii,27, 2806 (1957).

    Google Scholar 

  6. M. Hellin, M. Davidson, and F. Coussemant, Bull. Soc. Chim. France, 1890 (1966).

  7. V. P. Kheifets, V. P. Babukh, and G. K. Oparina, Zavodsk. Laboratoriya,34, No. 5, 529 (1968).

    Google Scholar 

  8. V. I. Kheifets, V. Z. Sharf, G. K. Oparina, M. K. Bychkova, V. P. Babukh, and L. Kh. Freidlin, Izv. Akad. Nauk SSSR, Ser. Khim., 1120 (1968).

  9. B. N. Bobylev, E. P. Tepenitsyna, and M. I. Farberov, Kinetika i Kataliz,9, 998 (1968); V. N. Bobylev, E. P. Tepenitsyna, and M. I. Farberov, Kinetika i Kataliz,10, 151 (1969).

    Google Scholar 

  10. J. Mawrin and E. Weisang, Bull. Soc. Chim. France, 3080 (1964).

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, Moscow

    V. Z. Sharf, V. I. Kheifets & L. Kh. Freidlin

Authors
  1. V. Z. Sharf
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. I. Kheifets
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. L. Kh. Freidlin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1761–1766, August, 1974.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sharf, V.Z., Kheifets, V.I. & Freidlin, L.K. Investigation of the stepwise mechanism of the acid-catalyzed condensation of 3-methyl-3-buten-1-ol with formaldehyde. Russ Chem Bull 23, 1681–1685 (1974). https://doi.org/10.1007/BF00923187

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00923187

Keywords

Search

Navigation