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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Authors: | O A Ivashkevich Vadim E Matulis A S Lyakhov I N Grigorieva P N Gaponik G T Sukhanov Yu V Filippova A G Sukhanova |
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Institution: | 1.Research Institute of Physical and Chemical Problems,Belarussian State University,Minsk,Belarus;2.Institute for Problems of Chemical and Energetic Technologies,Siberian Branch of the Russian Academy of Sciences,Biysk,Russia |
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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 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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