Rediscovering Cyanogen Gas for Organic Synthesis: Formation of 2-Cyanothiazole Derivatives

Prieschl, Michael; Sedelmeier, Joerg; Püntener, Kurt; Hildbrand, Stefan; Williams, Jason D.; Kappe, C. Oliver

doi:10.1021/acs.joc.3c01110

Cited by 5 publications

(2 citation statements)

References 33 publications

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“…While (CN) 2 finds some application as a fumigant and in organic synthesis, it forms HCN upon hydrolysis and also in vivo , resulting in an acute toxicity only slightly lower than that of HCN itself [74–76] . The observation of these gases challenges the perception of PBA/PW as being non‐toxic and raises safety concerns regarding SIBs using such CAMs.…”

Section: Introductionmentioning

confidence: 99%

“…[46,73] While (CN) 2 finds some application as a fumigant and in organic synthesis, it forms HCN upon hydrolysis and also in vivo, resulting in an acute toxicity only slightly lower than that of HCN itself. [74][75][76] The observation of these gases challenges the perception of PBA/PW as being non-toxic and raises safety concerns regarding SIBs using such CAMs. This is especially relevant when considering overcharge events, both intentional and unintentional, and application in confined and poorly ventilated spaces, as commonly found in stationary energystorage systems located in basements, server rooms, etc.…”

Section: Introductionmentioning

confidence: 99%

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Elucidating Gas Evolution of Prussian White Cathodes for Sodium‐ion Battery Application: The Effect of Electrolyte and Moisture

Dreyer,

Maddar,

Kondrakov

et al. 2024

Batteries & Supercaps

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As global energy storage demand increases, sodium‐ion batteries are often considered as an alternative to lithium‐ion batteries. Hexacyanoferrate cathodes, commonly referred to as Prussian blue analogues (PBAs), are of particular interest due their low‐cost synthesis and promising electrochemical response. However, because they consist of ~50 wt% cyanide anions, a possible release of highly toxic cyanide gases poses a significant safety risk. Previously, we observed the evolution of (CN)2 during cycling via differential electrochemical mass spectrometry (DEMS), but were unable to determine a root cause or mechanism. In this work, we present a systematical investigation of the gas evolution of Prussian white (PW) with different water content via DEMS. While H2 is the main gas detected, especially in hydrated PW and during overcharge (4.6 V vs. Na+/Na), the evolution of CO2 and (CN)2 depends on the electrolyte conductive salt. The use of oxidative NaClO4 instead of NaPF6 is the leading cause for the formation of (CN)2. Mass spectrometric evidence of trace amounts of HCN is also found, but to a much lower extent than (CN)2, which is the dominant safety risk when using NaClO4‐containing electrolyte. Despite being a good model salt, it is not a viable option for commercial applications.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Elucidating Gas Evolution of Prussian White Cathodes for Sodium‐ion Battery Application: The Effect of Electrolyte and Moisture

Dreyer,

Maddar,

Kondrakov

et al. 2024

Batteries & Supercaps

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Selective Hydrogenation of Unsaturated Vinyl Ethers in Two‐Chamber Gauge‐Reactor

Gyrdymova,

Saybulina,

Mironenko

et al. 2024

Asian J Org Chem

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A pressure gauge was incorporated into a two‐chamber glass H‐tube to continuously monitor the pressure inside a reactor when working with gases. The ex situ generated H2, D2, acetylene and CO2 were tested in pressure gauge reactors, and calibration curves were plotted. A series of unsaturated compounds with two or more double C=C bonds accessible for hydrogenation were synthesized for hydrogenation. The hydrogenation proceeded well due to constant pressure control, and the desired products were isolated in good yields. The same hydrogenation procedures were then carried out using steel autoclaves to verify the results and compare them. Surprisingly, almost the same results were obtained, confirming the effectiveness of self‐made glass reactors. The hydrogenation mechanism was further investigated using D‐labeled reagents. The kinetics of hydrogenation was studied both in manometric glass reactors and in steel autoclaves, which showed a similar nature of the main process in both reaction units. Thus, the created reactors can be effectively used in barometric transformations instead of steel autoclaves in appropriate cases.

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Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3+2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides

Zhang,

Chen,

Liu

et al. 2024

Asian J Org Chem

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We developed a novel method for the synthesis of 2‐substituted‐4,5‐dihydrothiazol‐4‐ols compounds through cyclization of thioamides and 1,4‐dithiane‐2,5‐diol in the presence of Et3N. Stable hydroxy‐substituted thiazole compounds were isolated of substituted thioamides. The reaction conditions are simple, the substrate range is wide, and the target compounds were obtained in up to 82% yield.

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Rediscovering Cyanogen Gas for Organic Synthesis: Formation of 2-Cyanothiazole Derivatives

Cited by 5 publications

References 33 publications

Elucidating Gas Evolution of Prussian White Cathodes for Sodium‐ion Battery Application: The Effect of Electrolyte and Moisture

Elucidating Gas Evolution of Prussian White Cathodes for Sodium‐ion Battery Application: The Effect of Electrolyte and Moisture

Selective Hydrogenation of Unsaturated Vinyl Ethers in Two‐Chamber Gauge‐Reactor

Synthesis of 2‐Substituted‐4,5‐Dihydrothiazol‐4‐Ols by [3+2] Annulation of 1,4‐Dithiane‐2,5‐Diol with Thioamides

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