Skip to main content
SpringerLink
Log in

Synthesis and some reactions of sulfides of the thiophene series

Communication 6. Action of sodium in liquid ammonia on acetals of 2-(ethylthio)- and 2-(benzylthio)-5-ethyl-3-thiophenecarboxaldehyde

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

Summary

  1. 1.

    By the action of sodium in liquid ammonia on diethyl acetals of 2-(alkylthio)-5-ethyl-3-thiophenecarboxaldehydes for the first time a member of a new class of bifunctional compounds containing a mercapto and an aldimine group of atoms in the molecule (VI) was prepared.

  2. 2.

    Some quadrifunctional derivatives of the thiophene series were prepared.

  3. 3.

    In the action of sodium in liquid ammonia on 2-(benzylthio)-5-ethyl-3-thiophenecarboxaldehyde diethyl acetal in addition to cleavage at the S-CH2C6H5 bond the elimination of the extracycle sulfur atom from the thiophene ring occurs.

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. P. Fridländer and E. Lenk, Ber.45, 2083 (1912); A. Wacek, H. Eppinger, and A. Bezar, Bér.,73, 52 (1940); R. Tzave, Farmaco Ed. scient.15, 468 (1960).

    Google Scholar 

  2. Y a. L. Gol'dfarb, M. A. Kalik,and M. L. Kirmalova, Izv. AN SSSR. Otd. khim. n. 1960, 1696.

  3. Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Zh. obshch. khimii30, 1012 (1960).

    Google Scholar 

  4. Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova, Zh. obshch. khimii29, 2034 (1959).

    Google Scholar 

  5. W. Fernelius and G. Watt, Chem. Revs20, 195 (1937); G. Hesseand I. Jörder, Ber.85, 924 (1952); W. Parham, G. Mayo, and B. Gadsby, J. Amer. Chem. Soc.,81, 5993 (1959).

    Google Scholar 

  6. C. Woster and J. Dean, J. Amer. Chem. Soc.,57, 112 (1935); A. Pinder and H. Smith, J. Chem. Soc., 1954, 113.

    Google Scholar 

  7. Ch. Hurd and L. Gersbein, J. Amer. Chem. Soc.,69, 2328 (1947).

    Google Scholar 

  8. H. Strain, J. Amer. Chem. Soc.,49, 1558 (1927).

    Google Scholar 

  9. E. Grishkevich-Trokhimovskii, Zh. Russk. fiz.-khim. obshch.43, 204 (1911).

    Google Scholar 

  10. W. Gordy and S. Stenford, J. Amer. Chem. Soc.,62, 497 (1940); S. Gronowitz, P. Moses, and A. Hörnfeldt, Arkiv. kemi17, 237 (1961).

    Google Scholar 

  11. Ya. L. Gol'dfarb and Yu. B. Vol'kenshtein, Dokl. AN SSSR128, 536 (1959).

    Google Scholar 

  12. S. Gronowitz, Arkiv. kemi,8, 441 (1955).

    Google Scholar 

  13. L. M. Shuter and B. Yu. Gordinskii, Zh. analit. khimii13, 150 (1958).

    Google Scholar 

  14. S. Gannizzaro and A. Rossi, Liebigs Ann. Chem.,121, 250 (1862).

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    Ya. L. Gol'dfarb, M. A. Kalik & M. L. Kirmalova

Authors
  1. Ya. L. Gol'dfarb
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. A. Kalik
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. L. Kirmalova
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Gol'dfarb, Y.L., Kalik, M.A. & Kirmalova, M.L. Synthesis and some reactions of sulfides of the thiophene series. Russ Chem Bull 11, 650–656 (1962). https://doi.org/10.1007/BF00904770

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00904770

Keywords

Search

Navigation