Skip to main content
Log in

Trifluoromethanesulfonic Hydrazides

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

We succeeded to observe at low temperature in reactions of trifluoromethanesulfonic anhydride and trifluoromethanesulfonyl chloride with hydrazine, phenyl hydrazine, and 1,1-dimethylhydrazine a formation of the corresponding trifluoromethanesulfonic hydrazides that at heating to room temperature decomposed liberating nitrogen and affording trifluoromethanesulfinic acid. 2-Phenyl-2H-1,2,3-triazole-4-carboxylic hydrazide reacted with trifluoromethanesulfonic anhydride to furnish trifluoro-N'-(2-phenyl-2H-1,2,3-triazol-4-ylcarbonyl)methane-sulfonic hydrazide that decomposed at heating with elimination of trifluoromethanesulfinic acid and nitrogen yielding 2-phenyl-2H-1,2,3-triazole-4-carbaldehyde.

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. Yagupol'skii, L.M., Kondratenko, N.V., Klare, Kh., Bezdudnyi, A.V., and Yagupol'skii, Yu.L., Zh. Org. Khim., 1999, vol. 35, p. 29.

    Google Scholar 

  2. Yagupol'skii, L.M., Kondratenko, N.V., and Iksanova, S.V., Zh. Org. Khim., 1995, vol. 31, p. 747.

    Google Scholar 

  3. Ying, W., DesMarteau, D.D., and Gotoh, Y., Tetrahedron, 1996, vol. 52, p. 15.

    Google Scholar 

  4. Xu, Y. and Zhu, S. Tetrahedron., 1999, vol. 55, p. 13725.

    Google Scholar 

  5. Xu, Y., Wang, Y., and Zhu, S., Synthesis, 2000, no. 4,p. 513.

  6. Roesky, H.W., Angew. Chem., 1971, vol. 83, p. 890.

    Google Scholar 

  7. Harzdorf, C., MeuIdoerffer, J-N., Niederprum, H., and Wechsberg, M., Lieb. Ann., 1973, p. 33.

  8. US Patent 2950317, 1960; Ref. Zh. Khim., 1961, 17L103.

  9. German Patent 2148597, 1973. Chem.Abstr., 1973, vol. 78, 158922.

  10. Hendrickson, J.B., Bair, K.W., Bergeron, R., Giga, A., Skipper, P. L., Sternbach, D.D., and Wareing, J.A., Org. Prep. Proc. Int., 1977, vol. 9, p. 173.

    Google Scholar 

  11. Hendrickson, J.B. and Sternbach, D.D., J. Org. Chem., 1975, vol. 40, p. 3450.

    Google Scholar 

  12. Haszeldine, R.N. and Kidd, J.M., J. Chem. Soc., 1955, no. 8, p. 2901.

  13. Fernandez, L.E., Ben, Altabef, A., Fantoni, A.C., and Varetti, E.L., Spectr. Acta, A, 1997, vol. 53, p. 189.

    Google Scholar 

  14. Dhar, M.L., Hughes, E.D., Ingold, C.K., Mandour, A.M.M., Maw, G.A., and Woolf, L.I., J. Chem. Soc., 1948, p. 2093.

  15. Overberger, C.J., Anselm, G.-P., and Lombardino, J.G., Organicheskie soedineniya so svyazyami azot.azot (Organic Componds with Nitrogen-Nitrogen Bonds), Leningrad: Khimiya, 1970.

    Google Scholar 

  16. Kuznetsov, M.A. and Ioffe, B.V., Zh. Obshch. Khim., 1977, vol. 47, p. 1627.

    Google Scholar 

  17. Larina, L.I., Karnaukhova, R.V., Nakhmanovich, A.S., Shagun, V. A., Ushakov, P.E., and Lopyrev, V.A., J. Mol. Struct., 2002, vol. 604, p. 165.

    Google Scholar 

  18. Riebsomer, J.L. and Sumrell, G., J. Org. Chem., 1948, vol. 13, p. 807.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shainyan, B.A., Tolstikova, L.L., Meshcheryakov, V.I. et al. Trifluoromethanesulfonic Hydrazides. Russian Journal of Organic Chemistry 40, 1071–1075 (2004). https://doi.org/10.1023/B:RUJO.0000045884.87574.ec

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUJO.0000045884.87574.ec

Keywords

Navigation