Synthesis and Properties of 1,3-Dialkyl-4-nitro-1,2,3-triazolium Salts
G. T. SUKHANOV1, YU. V. FILIPPOVA1, I. YU. BAGRYANSKAYA2, A. G. SUKHANOVA1, K. K. BOSOV1, I. A. KRUPNOVA1, E. V. PIVOVAROVA1
1Institute for Problems of Chemical and Energetic Technologies, Siberian Branch of the Russian Academy of Sciences, Biysk, Russia
2N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, Novosibirsk, Russia
Keywords: N-alkyl-4-nitro-1,2,3-triazoles, quaternization, regioselectivity, 1,3-dialkyl-4-nitro-1,2,3-triazolium salts, X-ray diffraction
Pages: 684-689
Abstract
A series of previously unknown 1,3-dialkyl-4-nitro-1,2,3-triazolium salts with the substituents of different kinds (alkyl = Me, Et, n -Pr, i -Pr, n -Bu, s -Bu, i -Amyl) were synthesized by regioselective quaternization of N2- and N3-alkyl-4-nitro-1,2,3-triazoles with dialkyl sulphates in a high yield. These salts are gaining an ever-growing interest in the chemistry of energetically efficient materials, catalysts and ionic liquids. Among the two regioisomers, solely N3-substituted derivatives were found to be involved in the reaction with dialkyl sulphates. The products of N2-substitution do not enter quaternization, and this fact makes it possible to separate the mixtures of N2- and N3-isomers that exhibit close physicochemical characteristics limiting their separation by preparative techniques. The structures of the new 1,3-dialkyl-4-nitro-1,2,3-triazolium salts were proved by means of IR spectroscopy, 1H and 13C NMR spectroscopy, as well as single-crystal X-ray diffraction and elemental analysis.
DOI: 10.15372/CSD2021349
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