Synthesis and Reactivity of Functionalized Tetrazenes: An Original Route Toward 1,2,3‐Triazoles

New alkyltetrazene structures with various terminal functional groups (hydroxyl, halogen, amine, hydrazine) basically in β ‐position were synthesized through the oxidation of their hydrazine precursors as novel ingredients for accessing nitrogen‐densified structures. To synthesize hydrazine‐ and amine‐substituted alkyltetrazenes, synthetic routes involving protection and deprotection steps were designed. In addition, β ‐activated alkyltetrazenes were obtained from their diol precursors, and their reactivity was investigated, resulting in a novel synthetic route of 1,2,3‐triazoles according to two complementary approaches. The scope was extended to β‐disubstituted derivatives, whose syntheses were also fully described.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2026-04-07
DOI
https://doi.org/10.1002/ejoc.202501179
Primary Topic
Synthesis of Tetrazole Derivatives
Type
article
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article

Synthesis and Reactivity of Functionalized Tetrazenes: An Original Route Toward 1,2,3‐Triazoles

Lionel Joucla, A. Renault, Chaza Darwich, John Eymann et al.
European Journal of Organic Chemistry
Synthesis of Tetrazole Derivatives
article

Synthesis and Reactivity of Functionalized Tetrazenes: An Original Route Toward 1,2,3‐Triazoles

Lionel Joucla, A. Renault, Chaza Darwich, John Eymann, Louis Le Moigne, Emmanuel Lacôte
article en

Abstract

New alkyltetrazene structures with various terminal functional groups (hydroxyl, halogen, amine, hydrazine) basically in β ‐position were synthesized through the oxidation of their hydrazine precursors as novel ingredients for accessing nitrogen‐densified structures. To synthesize hydrazine‐ and amine‐substituted alkyltetrazenes, synthetic routes involving protection and deprotection steps were designed. In addition, β ‐activated alkyltetrazenes were obtained from their diol precursors, and their reactivity was investigated, resulting in a novel synthetic route of 1,2,3‐triazoles according to two complementary approaches. The scope was extended to β‐disubstituted derivatives, whose syntheses were also fully described.

European Journal of Organic ChemistryVol. 29(17)
Université Claude Bernard Lyon 1 (FR), Centre National de la Recherche Scientifique (FR), Lyon College (US)
Openalex Percentile: Top 34%
Synthesis of Tetrazole Derivatives
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Synthesis and Reactivity of Functionalized Tetrazenes: An Original Route Toward 1,2,3‐Triazoles — Lionel Joucla, A. Renault, et al. · European Journal of Organic Chemistry (2026) | TGRS Research Map | TGRS