Trans-N-alkylation Covalent Exchanges on 1,3,4-Trisubstituted 1,2,3-Triazolium Iodides

被引:1
作者
Akacha, Rania [1 ,2 ]
Abdelhedi-Miladi, Imen [2 ]
Montarnal, Damien [3 ]
Ben Romdhane, Hatem [2 ]
Drockenmuller, Eric [1 ]
机构
[1] Univ Claude Bernard Lyon 1, Ingn Mat Polymeres, CNRS, UMR 5223, F-69622 Villeurbanne, France
[2] Univ Tunis El Manar, Fac Sci Tunis, Lab Chim Bio Organ Structurale & Polymeres Synth &, Manar, Tunis 2092, Tunisia
[3] Univ Claude Bernard Lyon 1, UMR 5128, CP2M, CNRS,Catalyse Polymerisat Procedes & Mat, F-69616 Villeurbanne, France
关键词
Ionic liquids; Kinetic study; Trans-N-alkylation; 1,2,3-Triazolium salts; Vitrimers; CLICK CHEMISTRY; ADAPTABLE NETWORKS; TRANSALKYLATION; POLYMER; ARCHITECTURES;
D O I
10.1002/ejoc.202300587
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
1,3,4-Trisubstituted 1,2,3-triazolium salts having either aliphatic or benzylic substituents at the N-1 and N-3 positions were synthesized in two steps involving: i) copper(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), and ii) N-alkylation of the 1,2,3-triazole intermediates. Trans-N-alkylation reactions in bulk and in the presence of excess methyl iodide were monitored by 1H NMR spectroscopy for each 1,2,3-triazolium molecular model. By assigning the different formed species and their respective evolution with time, it was possible to conclude that trans-N-alkylation exchange reactions are significantly faster for benzylic substituents than for aliphatic ones. Furthermore, the exchange reactions are noticeably faster at the N-3 position than at the N-1 position most likely due to the steric hindrance induced by the neighboring C-4 substituent. The kinetics of trans-N-alkylation reactions are thus influenced by both the chemical nature of the N-1 and N-3 substituents and the regiochemistry of the 1,2,3-triazolium group. This provides important structural design rules to improve the properties of thermosetting covalent adaptable networks involving trans-N-alkylation of 1,2,3-triazolium salts.
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页数:7
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