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Synlett 2013; 24(17): 2183-2187
DOI: 10.1055/s-0033-1339854
DOI: 10.1055/s-0033-1339854
synpacts
Recent Advanced Strategies for Extending the Nitrogen Chain in the Synthesis of High Nitrogen Compounds
Further Information
Publication History
Received: 08 June 2013
Accepted after revision: 26 August 2013
Publication Date:
20 September 2013 (online)
Abstract
The synthesis and handling of compounds containing long catenated nitrogen chains are challenging for researchers in this field. These challenges arise from their high endothermic, thermodynamic instability, and a serious lack of nitrogen–nitrogen bond-forming reactions. This paper addresses techniques of azo-coupling reaction between the diazonium salt of N-NH2 and amine derivative to form the longest nitrogen chain (N11). This type of nitrogen–nitrogen bond formation opens a new strategy for the construction of novel compounds containing odd or even numbers of catenated nitrogen atoms (≥9) especially for polynitrogen compounds.
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- 21 Typical Procedure A solution of NaNO2 (0.69 g, 10 mmol) in H2O (5 mL) was added dropwise to a stirring solution of DAT (1.0 g, 10 mmol) in concd HCl (5 mL). The reaction mixture was kept at 0 °C for 30 min. The crude residues obtained after the removal of the solvent under vacuum was treated with hot EtOH (20 mL) and then filtered to remove unsolvable salt. The filtrate was evaporated, dried, and recrystallized with EtOH to afford 0.5 g of needle crystals. 1H NMR (500 MHz, DMSO-d 6, 25 °C, TMS): δ = 7.93 ppm. 13C NMR (126 MHz, DMSO-d 6, 25 °C, TMS): δ = 153.8, 152.5, 150.1 ppm. IR: 3403 (m), 3193 (m), 3157 (m), 3056 (s), 1692 (s), 1640 (vs), 1578 (w), 1472 (vw), 1447 (w), 1274 (w), 1052 (w), 984 (w), 893 (w), 773 (w), 728 (w), 673 (w) cm–1. Raman: 1684, 1582, 1390, 1284, 1062, 746 cm–1. BAM impact: 10 J; BAM friction: 160 N; electrostatic sensitivity discharge (ESD): 0.32 J.