Study of the reactivity of 1,1’-dimethylbistetrazole towards catalytic hydrogenation and chemical reduction - Université Claude Bernard Lyon 1 Access content directly
Journal Articles Reaction kinetics, mechanisms and catalysis Year : 2021

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

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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Dates and versions

hal-03460647 , version 1 (01-12-2021)

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Teddy Gilloux, Guy Jacob, Emilie Labarthe, Henri Delalu, Chaza Darwich. Study of the reactivity of 1,1’-dimethylbistetrazole towards catalytic hydrogenation and chemical reduction. Reaction kinetics, mechanisms and catalysis, 2021, 134 (2), pp.851-865. ⟨10.1007/s11144-021-02118-1⟩. ⟨hal-03460647⟩
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