N-Alkylation of 4-nitro-1,2,3-triazole revisited. Detection and characterization of the N3-ethylation product, 1-ethyl-5-nitro-1,2,3-triazole

被引：24

作者：

Voitekhovich, Sergei V. ^{[1
]}

Gaponik, Pavel N. ^{[1
]}

Lyakhov, Alexander S. ^{[1
]}

Filipova, Juliya V. ^{[2
]}

Sukhanova, Anna G. ^{[2
]}

Sukhanov, Gennady T. ^{[2
]}

Ivashkevich, Oleg A. ^{[1
]}

机构：

[1] Belarusian State Univ, Res Inst Physicochem Problems, Minsk 220030, BELARUS

[2] Russian Acad Sci, Inst Problems Chem & Energet Technol, Siberian Branch, Biisk 659322, Russia

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 21期

关键词：

4-Nitro-1,2,3-triazole; Alkylation; X-ray analysis; Copper(II) complex; C-13; H-1;

D O I：

10.1016/j.tetlet.2009.03.076

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The products of the alkylation of sodium 4-nitro-1,2,3-triazolate with ethyl bromide were investigated using H-1, C-13, and N-15 NMR spectroscopy. It was found that alkylation proceeds on the triazole nitrogen atoms giving a mixture of three isomeric N-ethyl-4-nitro-1,2,3-triazoles. The molar ratio of N1, N2, and N3-alkylation products was 4:8:1. The formation of a minor N3-isomer, namely 1-ethyl-5-nitro-1,2,3-triazole was confirmed by X-ray structural analysis of single crystals of its tetranuclear copper(II) complex obtained by reaction of copper(II) chloride dihydrate with a mixture of the N2 and N3-isomers. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：2577 / 2579

页数：3

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