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Russian Journal of Organic Chemistry

, Volume 54, Issue 11, pp 1638–1642 | Cite as

Nitrimines: VII. Reaction of S,S′-Dimethyl-N-nitroimidodithiocarbonate with Alkali. Synthesis of S-Methyl-N-nitrothiocarbamate and Its Salts

  • A. M. AstakhovEmail author
  • D. V. Antishin
  • А. А. Nefedov
  • G. E. Salnikov
  • E. S. Buka
Article
  • 3 Downloads

Abstract

Reaction of S,S′-dimethyl-N-nitroimidodithiocarbonate with alkali in aqueous-alcoholic solution results in salts of S-methyl-N-nitrothiocarbamate. In anhydrous ethanol a salt of nitrouretane is obtained. By the reaction of S-methyl-N-nitrothiocarbamate salts with hydrazine 4-nitrosemicarbazide salts were prepared.

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References

  1. 1.
    Astakhov, A.M., Buka, E.S., and Revenko, V.A., Izv. Vuzov, Ser. Khim. Khim. Tekhnol., 2008, vol. 51, p. 26.Google Scholar
  2. 2.
    McKay, A.F., Chem. Rev., 1952, vol. 51, p. 301.CrossRefGoogle Scholar
  3. 3.
    Gao, H. and Shreeve, J.M., Chem. Rev., 2011, vol. 111, p. 7377.CrossRefGoogle Scholar
  4. 4.
    Fischer, D., Klapӧtke, T.M., and Stierstorfer, J., Proc. 15th Seminar “New Trends Res. Energ. Mat., (NTREM)”, University of Pardubice, Pardubice, Czech Republic, April 18–20, 2012, p. 1, p. 117.Google Scholar
  5. 5.
    Zhao, Y., Wang, G., Li, Y., Wang, S., and Li, Z., Chin. J. Chem., 2010, vol. 28, p. 475.CrossRefGoogle Scholar
  6. 6.
    Kagabu, S., Hibi, M., and Nishimura, K., Biosci. Biotechnol. Biochem., 2005, vol. 69, p. 705.CrossRefGoogle Scholar
  7. 7.
    Zhang, A., Kayser, H., Maienfisch, P., and Casida, J.E., J. Neurochem., 2000, vol. 75, p. 1294.CrossRefGoogle Scholar
  8. 8.
    Kovganko, N.V. and Kashkan, Zh.N., Russ. J. Org. Chem., 2004, vol. 40, p. 1709. doi  https://doi.org/10.1007/s11178-005-0089-y CrossRefGoogle Scholar
  9. 9.
    Wright, J.F., The Chemistry of the Nitro and Nitroso Groups, Feuer, H., Ed., New York: Intersci. Publ. 1969, vol. 1.Google Scholar
  10. 10.
    Kojima, S., Funabora, M., Kawahara, N., and Iiyoshi, Y., US Patent no. 5453529, 1990.Google Scholar
  11. 11.
    Fishbein, L. and Gallaghan, J.A., J. Am. Chem. Soc., 1954, vol. 76, p. 1877.CrossRefGoogle Scholar
  12. 12.
    Astakhov, A.M., Antishin, D.V., Revenko, V.A., Vasiliev, A.D., and Buka, E.S., Chem. Heterocycl. Compd., 2017, vol. 53, p. 722. doi  https://doi.org/10.1007/s10593-017-2116-7 CrossRefGoogle Scholar
  13. 13.
    Petrie, M.A., Bottaro, J.C., Penwell, P.E., and Dodge, A.L., US Patent Appl. no. 0139618, 2009.Google Scholar
  14. 14.
    Astachov, A.M., Kruglyakova, L.A., Gelemurzina, I.V., Vasiliev, A.D., and Stepanov, R.S., Proc. 16th Seminar “New Trends Res. Energ. Mat., (NTREM)”, University of Pardubice, Pardubice, Czech Republic, 2013, vol. 1, p. 36.Google Scholar
  15. 15.
    Shlyapochnikov, V.A., Kolebatel’nye spektry alifaticheskikh nitrosoedinenii (Vibrational Spectra of Aliphatic Nitrocompounds), Ivshin, V.P., Ed., Ioshkar-Ola: Izd. Udm. Gos. Iniv., 2007.Google Scholar
  16. 16.
    Morozova, N.S., Metelkina, E.L., Novikova, T.A., Shlyapochnikov, V.A., Sergienko, O.I., and Perekalin, V.V., Zh. Org. Khim., 1983, vol. 19, p. 1228.Google Scholar
  17. 17.
    Il’yasov, S.G., Lobanova, A.A., Popov, N.I., and Sataev, R.R., Russ. J. Org. Chem., 2002, vol. 38, p. 1731. doi  https://doi.org/10.1023/A:1022503310689 CrossRefGoogle Scholar
  18. 18.
    Il’yasov, S.G., Lobanova, A.A., Popov, N.I., Kazantsev, I.V., Varand, V.L., and Larionov, S.V., Russ. J. Gen. Chem., 2006, vol. 76, p. 1719. doi  https://doi.org/10.1134/S1070363206110077 CrossRefGoogle Scholar
  19. 19.
    Il’yasov, S.G., Sakovich, G.V., and Lobanova, A.A., Propellants Explos. Pyrotech., 2013, vol. 38, p. 327.CrossRefGoogle Scholar
  20. 20.
    Glukhacheva, V.S., Il’yasov, S.G., Sakovich, G.V., Tolstikova, T.G., Bryzgalov, A O., and Pleshkova, N.V., Russ. Chem. Bull., 2016, vol. 65, p. 550. doi  https://doi.org/10.1007/s11172-016-1336-9 CrossRefGoogle Scholar
  21. 21.
    Il’yasov, S.G. and Glukhacheva, V.S., Polzunov. Vestn., 2008, p. 51.Google Scholar
  22. 22.
    Il’yasov, S.G. and Glukhacheva, V.S., Polzunov. Vestn., 2013, p. 26.Google Scholar
  23. 23.
    Thiele, J. and Lachman, A., Lieb. Ann. Chem., 1895, vol. 288, p. 267.CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • A. M. Astakhov
    • 1
    Email author
  • D. V. Antishin
    • 1
  • А. А. Nefedov
    • 2
  • G. E. Salnikov
    • 2
  • E. S. Buka
    • 1
  1. 1.Reshetnev Siberian State University of Science and TechnologyKrasnoyarskRussia
  2. 2.Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian BranchRussian Academy of SciencesNovosibirskRussia

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