s-Tetrazine: Robust and Green Photoorganocatalyst for Aerobic Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones

Abstract

Efficient photocatalytic aerobic oxidative dehydrogenation reactions of N,N-disubstituted hydroxylamines to nitrones were developed with an in situ generated photocatalyst based on commercially available 3,6-dichlorotetrazine. This process affords a wide range of nitrones in high yields under mild conditions. In addition, an oxidative (3+3) cycloaddition between an oxyallyl cation precursor and a hydroxylamine was also developed.

Crystal engineering of high explosives through lone pair-π interactions: Insights for improving thermal safety

“…First, being an H,C,N-containing planar molecule with high N/C ratio, it is easily identified as an aromatic of choice for the development of high-energy materials, explosives, and pyrotechnics. 1 , 2 This does not exhaust s -tetrazine applications in material chemistry since it possesses a ring-centred π∗ lowest unoccupied molecular orbital (LUMO) and generally gives rise to reversible redox processes, making it appealing for new materials for energy storage, 3 oxidation photocatalysts, 4 , 5 , 6 polymer biosensors, 7 , 8 or molecular magnets 9 , 10 built from metal complexes of tetrazine anion radicals. It also finds applications as 2,3 diazadiene in inverse electron-demand Diels Alder reactions, making it attractive for organic synthesis 11 and metal-free biorthogonal chemistry 12 , 13 as well as the recently proposed photocatalytically activated orthogonal chemistry 14 that enable subcellular biomolecular labeling applications in living systems.…”

Balancing high energy density and chemical stability in redox flow batteries with symmetric tetrazines

“…s-Tetrazines (< 120-200 Da) are already known for their reversible electrochemical reductions and used in diverse applications, 47 including as electro(fluoro)chromic materials, 48,49 photocatalysts, 50,51,52,53,54 and components for solid-state batteries. 55,56 Here we explore their potential for redox flow batteries.…”