Russian Journal of Organic Chemistry

, Volume 43, Issue 8, pp 1213–1217 | Cite as

Synthesis of 1,2-diols ethers, condensation products of glyoxal with nitrogen-containing nucleophiles: I. Reaction of cyclic sulfites with primary alcohols and glycols

  • E. V. Sizova
  • V. V. SizovEmail author
  • I. V. Tselinskii


In reactions of 4,5-diacetoxy-2-(dinitromethylene)imidazolidine, 4,5-diacetoxy-2-nitriminoimidazolidine, and 1,2-diacetoxy-1,2-bis(chloroacetylamino)ethane with thionyl chloride at room temperature the corresponding cyclic sulfites were obtained. Treating the sulfites with methanol, ethanol, and 2-chloroethanol at room temperature we prepared acyclic ethers in 80–90% yields. Similarly cyclic ethers were synthesized from ethylene glycol and 1,3-propanediol in 50–60% yields.


Sulfite Glyoxal Thionyl Chloride Cyclic Ether Imidazolidine 
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  1. 1.
    Sizova, E.V., Sizov, V.V., and Tselinskii, I.V., Zh. Org. Khim., 2007, vol. 43, p. 1235.Google Scholar
  2. 2.
    Masaya, I. and Atsushi, M., Japan Patent 2000-159734, 2000; Chem. Abstr., 2000, vol. 133, 17467v.Google Scholar
  3. 3.
    Ota Seiyaku Co., Ltd., Japan Patent 58 103 343, 1981; Chem. Abstr., 1981, vol. 99, 122022y.Google Scholar
  4. 4.
    Bolotov, A.A., Rodin, A.A., V’yunov, K.A., Ginak, A.I., and Sarkisov, Yu.S., Zh. Org. Khim., 1982, vol. 18, p. 2060.Google Scholar
  5. 5.
    Bolotov, A.A., Rodin, A.A., V’yunov, K. A., and Ginak, A.I., Zh. Org. Khim., 1984, vol. 20, p. 1185.Google Scholar
  6. 6.
    Azuma, N., Takata, T., Sanda, F., and Endo, T. Macromolecules, 1995, vol. 28, p. 7331.CrossRefGoogle Scholar
  7. 7.
    Van Woenden, H.F. Chem. Rev., 1963, vol. 63, no. 6, p. 557.CrossRefGoogle Scholar
  8. 8.
    Vail, S.L., Moran, C.M., and Barker, R.H., J. Org. Chem., 1965, vol. 30, p. 1195.CrossRefGoogle Scholar
  9. 9.
    Tanimoto, S., Imazu, Y., Imuta, M., and Okano, M., Bull. Inst. Chem. Res., Kyoto, Univ., 1972, vol. 50, no. 4, p. 368.Google Scholar
  10. 10.
    Terpigorev, A.N. and Rudakova, S.B., Zh. Org. Khim., 1998, vol. 34, p. 1078.Google Scholar
  11. 11.
    Sizova, E.V., Sizov, V.V., Zelenov, M.P., and Tselinskii, I.V., Zh. Org. Khim., 2007, vol. 43, p. 178.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • E. V. Sizova
    • 1
  • V. V. Sizov
    • 1
    Email author
  • I. V. Tselinskii
    • 1
  1. 1.St. Petersburg State Technological InstituteSt. PetersburgRussia

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