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.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Astakhov, A.M., Buka, E.S., and Revenko, V.A., Izv. Vuzov, Ser. Khim. Khim. Tekhnol., 2008, vol. 51, p. 26.
McKay, A.F., Chem. Rev., 1952, vol. 51, p. 301.
Gao, H. and Shreeve, J.M., Chem. Rev., 2011, vol. 111, p. 7377.
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.
Zhao, Y., Wang, G., Li, Y., Wang, S., and Li, Z., Chin. J. Chem., 2010, vol. 28, p. 475.
Kagabu, S., Hibi, M., and Nishimura, K., Biosci. Biotechnol. Biochem., 2005, vol. 69, p. 705.
Zhang, A., Kayser, H., Maienfisch, P., and Casida, J.E., J. Neurochem., 2000, vol. 75, p. 1294.
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
Wright, J.F., The Chemistry of the Nitro and Nitroso Groups, Feuer, H., Ed., New York: Intersci. Publ. 1969, vol. 1.
Kojima, S., Funabora, M., Kawahara, N., and Iiyoshi, Y., US Patent no. 5453529, 1990.
Fishbein, L. and Gallaghan, J.A., J. Am. Chem. Soc., 1954, vol. 76, p. 1877.
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
Petrie, M.A., Bottaro, J.C., Penwell, P.E., and Dodge, A.L., US Patent Appl. no. 0139618, 2009.
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.
Shlyapochnikov, V.A., Kolebatel’nye spektry alifaticheskikh nitrosoedinenii (Vibrational Spectra of Aliphatic Nitrocompounds), Ivshin, V.P., Ed., Ioshkar-Ola: Izd. Udm. Gos. Iniv., 2007.
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.
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
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
Il’yasov, S.G., Sakovich, G.V., and Lobanova, A.A., Propellants Explos. Pyrotech., 2013, vol. 38, p. 327.
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
Il’yasov, S.G. and Glukhacheva, V.S., Polzunov. Vestn., 2008, p. 51.
Il’yasov, S.G. and Glukhacheva, V.S., Polzunov. Vestn., 2013, p. 26.
Thiele, J. and Lachman, A., Lieb. Ann. Chem., 1895, vol. 288, p. 267.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © A.M. Astakhov, D.V. Antishin, А.А. Nefedov, G.E. Salnikov, E.S. Buka, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 11, pp. 1629–1633.
For communication VI, see [1].
Rights and permissions
About this article
Cite this article
Astakhov, A.M., Antishin, D.V., Nefedov, А.А. et al. Nitrimines: VII. Reaction of S,S′-Dimethyl-N-nitroimidodithiocarbonate with Alkali. Synthesis of S-Methyl-N-nitrothiocarbamate and Its Salts. Russ J Org Chem 54, 1638–1642 (2018). https://doi.org/10.1134/S1070428018110039
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428018110039