SELECTIVE SYNTHESIS OF 1,3-DIALKYL-4-NITRO-1,2,3-TRIAZOLIUM SALTS FROM 1-ALKYL-4-NITRO-1,2,3-TRIAZOLES AND DIALKYL SULFATES

Authors

  • О. А. Ивашкевич Research Institute of Physical and Chemical Problems, Belarussian State University, Minsk 22030
  • Вадим Э. Матулис Research Institute of Physical and Chemical Problems, Belarussian State University, Minsk 22030
  • А. С. Ляхов Research Institute of Physical and Chemical Problems, Belarussian State University, Minsk 22030
  • И. Н. Григорьева Research Institute of Physical and Chemical Problems, Belarussian State University, Minsk 22030
  • П. Н. Гапоник Research Institute of Physical and Chemical Problems, Belarussian State University, Minsk 22030
  • Г. Т. Суханов Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, Biysk 659322
  • Ю. В. Филиппова Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, Biysk 659322
  • А. Г. Суханова Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, Biysk 659322

DOI:

https://doi.org/10.1007/6561

Keywords:

C-nitro-1, 2, 3-triazoles, 3-triazolium salts, quantum-chemical calculations, quaternization, X-ray crystallography

Abstract

The process of alkylation of 1-alkyl-substituted 4-nitro-1,2,3-triazoles with dimethyl and diethyl sulfates has been studied. The structures of the N,N’-dialkyl-C-nitro-1,2,3-triazolium alkylsulfates and perchlorates has been confirmed by IR,  1H and  13C NMR spectroscopy. Alkylation with an excess of dialkyl sulfate occurred regioselectively at N-3 with the formation of 1,3-dialkyl-4-nitro-1,2,3-triazolium salts, which is in agreement quantum-chemical calculations of the relative stability of the corresponding isomeric cations. The molecular and crystal structures  of the first example of this type of salt – 1,3-diethyl-4-nitro-1,2,3-triazolium perchlorate  – have been determined by X-ray crystallography. Nitrotriazolium salts with mixed alkyl substituents – 3-ethyl-1-methyl- and 1-ethyl-3-methyl-4-nitro-1,2,3-triazolium salts – have been synthesized an studied for the first time.

How to Cite
Ivashkevich, O. A.; Matulis, Vadim E.; Lyakhov, A. S.; Grigorieva, I. N.; Gaponik, P. N.; Sukhanov, G. T.; Filippova, Yu. V.; Sukhanova, A. G.  Chem. Heterocycl. Compd. 2009, 45, 1218. [Khim. Geterotsikl. Soedin. 2009, 1519.]

For this article in the English edition see DOI 10.1007/s10593-010-0410-8



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Published

2022-02-10

Issue

No. 10 (2009)

Section

Original Papers