Chemistry of Heterocyclic Compounds

, Volume 32, Issue 2, pp 169–173 | Cite as

Synthesis of 2-phenylethynyl-1,3-dioxanes and their hydrolysis

  • T. P. Kosulina
  • V. G. Kul'nevich


2-Phenylethynyl substituted 1,3-dioxanes were obtained by the reaction of 1,3-dioxanium salts with an lotsich reagent. It was shown that they are readily hydrolyzed with the formation of a-acerylenic ketones. A simple new method is proposed for the synthesis of the latter without isolating the intermediate 1,3-dioxanes using the reaction of 4 substituted 2-methyl(phenyl, furyl)-1,3-dioxanium salts with hydroxymethyl- and phenylethynylmagnesium bromide as examples.


Hydrolysis Bromide Organic Chemistry Phenyl Ketone 
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  1. 1.
    K. J. H. Kruithof, R. P. Schmitz, and G. W. Klumpp, Tetrahedron,39, 3073 (1983).Google Scholar
  2. 2.
    D. L. Rakhmankulov, R. A. Karakhanov, S. S. Zlotskii, E. A. Kantor. U. B. Imashev, and A. M. Syrkin, Progress in Science and Technology [in Russian], Vol. 5 (1975), p. 288.Google Scholar
  3. 3.
    Z. I. Zelikman, T. P. Kosulina, V. G. Kul'nevich, and B. A. Tertov, USSR Author's Certificate 596,586; Byull. Izobret., No. 9, 51 (1973).Google Scholar
  4. 4.
    Z. I. Zelikman, Yu. Yu. Samitov, T. P. Kosulina, V. G. Kul'enevich, and B. A. Tertov, Khim. Geterotsikl. Soedin., No. 9, 1172 (1978).Google Scholar
  5. 5.
    Z. I. Zelikman, T. P. Kosulina, V. G. Kul'nevich, G. N. Dorofeenko, and L. V. Mezheritskaya, Khim. Geterotsikl. Soedin., No. 2, 169 (1976).'Google Scholar
  6. 6.
    T. P. Kosulina, E. V. Gromachevskaya, L. A. Falina, A. G. Kolesnikov, and V. G. Kul'nevich, Khim. Geterotsikl. Soedin., No. 4, 464 (1983).Google Scholar
  7. 7.
    Z. I. Zelikman, T. P. Kosulina, and V. G. Kul'nevich, USSR Author's Certificate 583,616; Byull. Izobret., No. 5, 40 (1976).Google Scholar
  8. 8.
    A. A. Polyakova and R. A. Khmel'nitskii, Mass Spectrometry in Organic Chemistry [in Russian], Khimiya, Moscow (1972), p. 138.Google Scholar
  9. 9.
    R. Johnstone, Handbook of Mass Spectrometry for Organic Chemists [Russian translation], Mir, Moscow (1975).Google Scholar
  10. 10.
    A. V. Shchelkunov and V. M. Rofman, Chemical-Metallurgical Institute, Academy of Sciences of the Kazakh SSR [in Russian], Moscow (1983), Deposited in VINITI, April 12, 1983, No. 2208-83.Google Scholar
  11. 11.
    T. P. Kosulina and V. G. Kul'nevich, USSR Author's Certificate 1,601,097; Byull. Izobret., No. 39, 97 (1990).Google Scholar
  12. 12.
    R. 1. Katkevich and L. I. Vereshchagin, Usp. Khim.,38, 1964 (1969).Google Scholar
  13. 13.
    D. Nightingale and F. T. Wadsworth, J. Am. Chem. Soc.,69, 1181 (1947).Google Scholar
  14. 14.
    B. J. W. Kroeger and J. A. Nieuwland, J. Am. Chem. Soc.,58, 1861 (1936).Google Scholar
  15. 15.
    S. Durantis and C. Balsamini, Synthesis, No. 5, 357 (1974).Google Scholar
  16. 16.
    A. M. Sladkov and I. R. Golding, Zh. Org. Khim.,3, 1338 (1967).Google Scholar
  17. 17.
    S. A. Giller, L. I. Vereshchagin, K. K. Venter, S. P. Korshunov, V. V. Tsirule, and D. O. Lolya, Dokl. Akad. Nauk SSSR,164, 98 (1965).Google Scholar

Copyright information

© Plenum Publishing Corporation 1996

Authors and Affiliations

  • T. P. Kosulina
    • 1
  • V. G. Kul'nevich
    • 1
  1. 1.Kuban State Technological UniversityKrasnodar

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