Skip to main content
SpringerLink
Log in

Geminal systems. Communication 28 Alcoholysis of N-chloro-N-alkoxyamides and synthesis of N,N-dialkoxyureas

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

Conclusions

  1. 1.

    N-Chloro-N-alkoxysulfonamides and N-chloro-N-alkoxyphosphoamides have chlorinating properties in the reaction with triethylamine in methanol.

  2. 2.

    N-Chloro-N-alkoxyureas were synthesized for the first time, and from them previously unknown N,N-dialkoxyureas were obtained by nucleophilic substitution reactions.

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. O. G. Nabiev, N. A.-G. Shakhgel'diev, I. I. Chervin, and R. G. Kostyanovskii, Dokl. Akad. Nauk SSSR,284, 872 (1985).

    Google Scholar 

  2. R. A. Falk and J. D. Readio, J. Org. Chem.,34, 4088 (1969); J. D. Readio and R. A. Falk, J. Org. Chem.,35, 927 (1970); J. D. Readio, J. Org. Chem.,35, 1607 (1970).

    Google Scholar 

  3. T. Koenig, J. A. Hoobler, and W. R. Mobey, J. Am. Chem. Soc.,94, 2514 (1972).

    Google Scholar 

  4. A. Zwierzak and J. Brykikowska, Synthesis, 712 (1975).

  5. H. Teeninga and J. B. F. N. Engberts, Recl. Trav. Chim.,97, 59 (1978).

    Google Scholar 

  6. V. G. Shtamburg, V. F. Rudchenko, Sh. S. Nasibov, I. I. Chervin, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 449 (1981).

  7. V. F. Rudchenko, I. I. Chervin, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 924 (1979); R. G. Kostyanovsky, V. F. Rudchenko, V. F. Shtamburg, I. I. Chervin, and Sh. S. Nasibov, Tetrahedron,37, 4245 (1981); V. G. Shtamburg, V. F. Rudchenko, Sh. S. Nasibov, I. I. Chervin, A. P. Pleshkova, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2320, 2327 (1981).

  8. V. F. Rudchenko, V. G. Shtamburg, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1183 (1981).

  9. K. Müller, Helv. Chim. Acta,53, 1112 (1970).

    Google Scholar 

  10. G. V. Shustov, A. V. Zoloti, and R. G. Kostyanovsky, Tetrahedron,38, 2319 (1982).

    Google Scholar 

  11. R. E. White and P. Covacic, J. Am. Chem. Soc.,97, 1180 (1975).

    Google Scholar 

  12. D. Graus, T. Clark, and P. V. R. Schleyer, Tetrahedron Lett.,21, 3681 (1980).

    Google Scholar 

  13. V. F. Rudchenko, V. I. Shevchenko, S. M. Ignatov, and R. G. Kostyanovskii, Izv. Akad. Nauk SSSR, Ser. Khim., 2411 (1983).

  14. A. V. Fokin and Yu. M. Kosyrev, Usp. Khim.,35, 1897 (1966).

    Google Scholar 

  15. Houben-Weyl, Methoden der Organische Chemie, Georg Tieme Verlag, Stuttgart, Vol. X/1 (1971), p. 1184.

  16. A. Rougny and M. Daudon, Bull. Soc. Chim. France, 833 (1976).

  17. R. M. Khomutov, Zh. Obshch. Khim.,31, 1992 (1961).

    Google Scholar 

  18. G. Zinner and W. Rolling, Arch. Pharm.,293/65, 82 (1960).

    Google Scholar 

  19. B. Loew and J. T. Massengale, J. Org. Chem.,22, 1186 (1957).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Chemical Physics, Academy of Sciences of the USSR, Moscow

    V. F. Rudchenko, V. I. Shevchenko & R. G. Kostyanovskii

Authors
  1. V. F. Rudchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. I. Shevchenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. R. G. Kostyanovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 598–606, March, 1986.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rudchenko, V.F., Shevchenko, V.I. & Kostyanovskii, R.G. Geminal systems. Communication 28 Alcoholysis of N-chloro-N-alkoxyamides and synthesis of N,N-dialkoxyureas. Russ Chem Bull 35, 543–551 (1986). https://doi.org/10.1007/BF00953222

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00953222

Keywords

Search

Navigation