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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

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Chemistry of Heterocyclic Compounds Aims and scope

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 crystallo-graphy. 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.

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Authors and Affiliations

  1. Research Institute of Physical and Chemical Problems, Belarussian State University, Minsk, 22030, Belarus

    O. A. Ivashkevich, Vadim E. Matulis, A. S. Lyakhov, I. N. Grigorieva & P. N. Gaponik

  2. Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, Biysk, 659322, Russia

    G. T. Sukhanov, Yu. V. Filippova & A. G. Sukhanova

Authors
  1. O. A. Ivashkevich
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  2. Vadim E. Matulis
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  3. A. S. Lyakhov
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  4. I. N. Grigorieva
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  5. P. N. Gaponik
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  6. G. T. Sukhanov
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  7. Yu. V. Filippova
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  8. A. G. Sukhanova
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Correspondence to Vadim E. Matulis.

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Translated from Khimiya Geterotsiklicheskikh Soedineneii, Number 10, 1519-1528, October, 2009.

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Ivashkevich, O.A., Matulis, V.E., Lyakhov, A.S. et al. 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. Chem Heterocycl Comp 45, 1218–1225 (2009). https://doi.org/10.1007/s10593-010-0410-8

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  • DOI: https://doi.org/10.1007/s10593-010-0410-8

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