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Study of the reactivity of 1,1’-dimethylbistetrazole towards catalytic hydrogenation and chemical reduction

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Abstract

Investigating the possibility of a straightforward formation of tetrazoline or tetrazolidine structures, the reactivity of a tetrazole derivative towards reducing conditions has been studied. The catalytic hydrogenation of 1,1’-dimethylbistetrazole (DMBT) was carried out using various catalysts (Pd/C, Pt/C, Rh/C, Pd/Pt/C, Lindlar, PtO2 and Raney Ni) over a wide range of hydrogen pressure (35–150 bar) and a temperature range from 20 to 60 °C. This exhaustive study enabled to find the optimal conditions for DMBT hydrogenation and to suggest a plausible reaction mechanism. The chemical reduction of DMBT was conducted using several hydrides (BH3, NaBH4, DIBAL and LiAlH4). The reduction products were identified subsequently to conditions optimizing. The suggested reaction mechanism, featuring a retro-[3 + 2]-cycloaddition, was validated by both experimental and theoretical approaches.

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Acknowledgements

Financial support by CNES, ArianeGroup, CNRS and Université Claude Bernard Lyon 1 is gratefully acknowledged.

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Authors and Affiliations

  1. Univ Lyon, Univ Claude Bernard Lyon 1, CNRS, CNES, ArianeGroup, LHCEP, UMR 5278, Bât. Raulin, 2 rue Victor Grignard, 69622, Villeurbanne, France

    Teddy Gilloux, Guy Jacob, Henri Delalu & Chaza Darwich

  2. ArianeGroup, Centre de Recherches du Bouchet, 9 rue Lavoisier, 91710, Vert-Le-Petit, France

    Guy Jacob

  3. CNES, Direction des Lanceurs, SDT Equipements Propulsifs et Mécanismes, 52 rue Jacques Hillairet, 75012, Paris, France

    Emilie Labarthe

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  1. Teddy Gilloux
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  2. Guy Jacob
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  3. Emilie Labarthe
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  4. Henri Delalu
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  5. Chaza Darwich
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Correspondence to Chaza Darwich.

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Gilloux, T., Jacob, G., Labarthe, E. et al. Study of the reactivity of 1,1’-dimethylbistetrazole towards catalytic hydrogenation and chemical reduction. Reac Kinet Mech Cat 134, 851–865 (2021). https://doi.org/10.1007/s11144-021-02118-1

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  • DOI: https://doi.org/10.1007/s11144-021-02118-1

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