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Chemistry of Heterocyclic Compounds

, Volume 4, Issue 4, pp 457–458 | Cite as

An investigation of the dehydration of 3-oxa-, 3-thia- and 3-aza-1,5-pentanediols in the presence of tricalcium phosphate

  • V. Z. Sharf
  • L. Kh. Freidlin
  • A. S. Nekrasov
  • A. A. Nazaryan
  • S. A. Ponomareva
Article
  • 24 Downloads

Abstract

In the presence of tricalcium phosphate, 3-oxa-, 3-aza-, and 3-thia-1, 5-pentanediols undergo intramolecular dehydration with the formation of heterocycles and also of unstable readily-polymerizing vinyl compounds. The total degree of conversion of the diols rises in the sequence diethyleneglycol <1, 5-pentanediol <diethanolamine <N-methylethanolamine <di(hydroxyethyl) sulfide. At low temperatures, the yield of cyclic product from 1, 5-pentanediol and diethyleneglycol is close to the degree of conversion of the diol, and at high temperatures it falls behind markedly. Diethanolamine, N-methyldiethanolamine, and di(hydroxyethyl) sulfide dehydrate to the corresponding six-membered oxides unselectively.

Keywords

Oxide Phosphate Sulfide Organic Chemistry Dehydration 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    L. Kh. Freidlin and V. Z. Sharf, 136, 1108, 1961.Google Scholar
  2. 2.
    L. Kh. Freidlin, V. Z. Sharf, G. I. Samokhvalov, M. A. Miropol'skaya, I. M. Privalova, and M. I. Yanotovskii, Neftekhimiya, 3, 104, 1963.Google Scholar
  3. 3.
    V. Z. Sharf, L. Kh. Freidlin, A. S. Nekrasov, I. V. Sablina, and A. A. Nazaryan, Neftekhimiya, 6, 407, 1966.Google Scholar
  4. 4.
    Yu. K. Yur'ev, K. Yu, Novitskii, and E. V. Kukharskaya, DAN, 68, 541, 1949.Google Scholar
  5. 5.
    R. D. Obolentsev and N. N. Gryazev, DAN, 73, 319, 1950.Google Scholar
  6. 6.
    U.S. patent 2777846, 1957; C.A. 51, 8810, 1957.Google Scholar
  7. 7.
    E. Frammu and B. Ungar, Ber., 56, 2286, 1957.Google Scholar
  8. 8.
    E. Swistaak, C.r., 240, 1544, 1545, 1955.Google Scholar
  9. 9.
    L. Kh. Freidlin and V. Z. Sharf, Kin. i kat., 1, 245, 1960.Google Scholar
  10. 10.
    V. Z. Sharf, L. V. Andreev, S. A. Ponomareva, and A. A. Nazaryan, Neftekhimiya, 7, 314, 1967.Google Scholar

Copyright information

© Consultants Bureau 1971

Authors and Affiliations

  • V. Z. Sharf
    • 1
    • 2
  • L. Kh. Freidlin
    • 1
    • 2
  • A. S. Nekrasov
    • 1
    • 2
  • A. A. Nazaryan
    • 1
    • 2
  • S. A. Ponomareva
    • 1
    • 2
  1. 1.Zelinskii Institute of Organic ChemistryAS USSRUSSR
  2. 2.Lomonosov Moscow Institute of Fine Chemical TechnologyUSSR

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