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

Akacha, Rania
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Univ Claude Bernard Lyon 1, Ingn Mat Polymeres, CNRS, UMR 5223, F-69622 Villeurbanne, France
Univ Tunis El Manar, Fac Sci Tunis, Lab Chim Bio Organ Structurale & Polymeres Synth &, Manar, Tunis 2092, Tunisia Univ Claude Bernard Lyon 1, Ingn Mat Polymeres, CNRS, UMR 5223, F-69622 Villeurbanne, France

Abdelhedi-Miladi, Imen
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Univ Tunis El Manar, Fac Sci Tunis, Lab Chim Bio Organ Structurale & Polymeres Synth &, Manar, Tunis 2092, Tunisia Univ Claude Bernard Lyon 1, Ingn Mat Polymeres, CNRS, UMR 5223, F-69622 Villeurbanne, France

Montarnal, Damien
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Univ Claude Bernard Lyon 1, UMR 5128, CP2M, CNRS,Catalyse Polymerisat Procedes & Mat, F-69616 Villeurbanne, France Univ Claude Bernard Lyon 1, Ingn Mat Polymeres, CNRS, UMR 5223, F-69622 Villeurbanne, France

Ben Romdhane, Hatem
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Univ Tunis El Manar, Fac Sci Tunis, Lab Chim Bio Organ Structurale & Polymeres Synth &, Manar, Tunis 2092, Tunisia Univ Claude Bernard Lyon 1, Ingn Mat Polymeres, CNRS, UMR 5223, F-69622 Villeurbanne, France

Drockenmuller, Eric
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Univ Claude Bernard Lyon 1, Ingn Mat Polymeres, CNRS, UMR 5223, F-69622 Villeurbanne, France Univ Claude Bernard Lyon 1, Ingn Mat Polymeres, CNRS, UMR 5223, F-69622 Villeurbanne, France
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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