Safe and practical ex-situ chlorination of electronically diverse π-systems

Aguilar, Glen C.; Lis, Patrycja A.; Wise, Dan E.; Martinez, Jenny S.; Parasram, Marvin

doi:10.1016/j.tetlet.2023.154591

Tetrahedron Letters

2023

DOI: 10.1016/j.tetlet.2023.154591

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Safe and practical ex-situ chlorination of electronically diverse π-systems

Glen C. Aguilar,

Patrycja A. Lis,

Dan E. Wise

et al.

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2024

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Cited by 2 publications

References 30 publications

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

Gyrdymova,

Saybulina,

Mironenko

et al. 2024

Asian J Org Chem

View full text Add to dashboard Cite

show abstract

Preparation of Sulfonyl Chlorides by Oxidative Chlorination of Thiols and Disulfides using HNO₃/HCl/O₂ in a Flow Reactor

Sulzer,

Polterauer,

Hone

et al. 2024

ChemSusChem

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A continuous flow metal‐free protocol for the synthesis of sulfonyl chlorides from thiols and disulfides in the presence of nitric acid, hydrochloric acid and oxygen was developed. The influence of the reaction parameters was investigated under batch and flow conditions. Online 19F NMR was successfully implemented to investigate different reaction conditions within a single experiment. The sulfonyl chlorides were isolated (mostly in 70‐81% yield) after performing a simple aqueous washing procedure. In particular, the protocol was successfully operated for >6 hours to convert phenyl disulfide to its corresponding sulfonyl chloride, achieving a throughput of 3.7 g h‐1. The environmental impact of the protocol was assessed and compared to an existing continuous flow protocol using 1,3‐dichloro‐5,5‐dimethylhydantoin (DCH) as reagent. The process mass intensity (PMI) for the newly‐developed flow protocol (15) compared favorably to the DCH flow process (20).

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Safe and practical ex-situ chlorination of electronically diverse π-systems

Cited by 2 publications

References 30 publications

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

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

Preparation of Sulfonyl Chlorides by Oxidative Chlorination of Thiols and Disulfides using HNO₃/HCl/O₂ in a Flow Reactor

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Safe and practical ex-situ chlorination of electronically diverse π-systems

Cited by 2 publications

References 30 publications

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

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

Preparation of Sulfonyl Chlorides by Oxidative Chlorination of Thiols and Disulfides using HNO3/HCl/O2 in a Flow Reactor

Contact Info

Product

Resources

About

Preparation of Sulfonyl Chlorides by Oxidative Chlorination of Thiols and Disulfides using HNO₃/HCl/O₂ in a Flow Reactor