Skip to main content
Log in

Tautomerism and vapor-phase transformations of 2-hydroxytetrahydrofuran

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The relative stability of 2-hydroxytetrahydrofuran and the tautomeric 4-hydroxybutanal was determined by the semi-empirical AM1 method. It was concluded that the cyclic tautomer predominates in the gas phase at 25°C. Vapor-phase dehydration of 2-hydroxytetrahydrofuran in the presence of porcelain and silica gel L leads to a quantitative yield of 2,3-dihydrofuran.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. R. Valters and W. Flitsch,Ring-Chain Tautomerism, Plenum Press, New York (1985), p. 100.

    Google Scholar 

  2. C. D. Hurd and W. H. Saunders,J. Am. Chem. Soc.,74, 5324 (1952).

    Google Scholar 

  3. C. Ögretir and M. Yaman,J. Mol. Struct. (Theochem),458, 217 (1999).

    Google Scholar 

  4. A. P. Khvorov,Author's Abstract of Thesis for Candidate of Chemical Sciences [in Russian], Leningrad (1983).

  5. L. Leite, S. Kruc, Zh. Yuskovets, V. Stonkus, M. Fleisher, E. Lukevics, J. Stoch, and M. Mikolayczyk, in:Studies in Surface Science and Catalysis (Eds. H. U. Blaser, A. Baiker, and R. Prins), Elsevier Science Publishers Co., Amsterdam,108, 641 (1997).

    Google Scholar 

  6. J. W. Kang and W. L. Hergenrother, Ger. Offen 2649900;Chem. Abstr.,87, 135015 (1977).

    Google Scholar 

  7. P. Dimroth and H. Pasedach,Angew. Chem.,72, 865 (1960).

    Google Scholar 

  8. M. Bartok and A. Molnar, in:The Chemistry of Ethers, Crown Ethers, Hydroxyl Groups and their Sulfur Analogues. Suppl. E2. Dehydration of Diols (Ed. S. Patai), Wiley and Sons, New York,16, 721 (1980).

    Google Scholar 

  9. I. I. Geiman, L. F. Bulenkova, A. A. Lazdin'sh, A. K. Veinberg, V. A. Slavinskaya, and A. A. Avots,Khim. Geterotsikl. Soedin., No. 4, 448 (1981).

    Google Scholar 

  10. L. Leite, A. Lebedevs, V. Stonkus, and M. Fleisher,J. Mol. Cat.,144, 323 (1999).

    Google Scholar 

  11. M. A. Makarova, E. A. Paushtis, J. M. Thomas, C. Williams, and K. I. Zamaraev,J. Catal.,149, 36 (1994).

    Google Scholar 

  12. Yu. Shinobara, T. Nakajima, S. Suzuki, S. Mishima, and H. Ishikawa,J. Chem. Software,4, No. 3, 89 (1997).

    Google Scholar 

  13. G. Swain and J. Brown,J. Am. Chem. Soc.,74, 2534 (1952).

    Google Scholar 

  14. J. J. P. Stewart,Program Package MOPAC (OCPE N 455), Version 5.0.

  15. Yu. I. Gorlov, V. A. Zaets, and A. A. Chuiko,Teor Eksp. Khim., No. 4, 407 (1988).

    Google Scholar 

  16. P. Ya. Gokhberg, V. A. Tolstonogov, and B. I. No,Kinet. Katal.,30, No. 2, 334 (1989).

    Google Scholar 

  17. L. Forni,Catal. Rev.,8, No. 1, 65 (1973).

    Google Scholar 

Download references

Authors

Additional information

Latvian Institute of Organic Synthesis, Riga, Latvia; e-mail: manton@osi.lv. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 885–889, July, 2000.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lebedev, A., Leite, L., Fleisher, M. et al. Tautomerism and vapor-phase transformations of 2-hydroxytetrahydrofuran. Chem Heterocycl Compd 36, 775–778 (2000). https://doi.org/10.1007/BF02256908

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02256908

Keywords

Navigation