Amine Induced Retardation of the Radical-Mediated Thiol–Ene Reaction via the Formation of Metastable Disulfide Radical Anions
| Autor: | John Taylor Goodrich, Benjamin D. Fairbanks, Dillon M. Love, Brady T. Worrell, Mark P. Stoykovich, Charles B. Musgrave, Christopher N. Bowman, Kangmin Kim |
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| Rok vydání: | 2018 |
| Předmět: |
chemistry.chemical_classification
Thiol-ene reaction Chemistry Radical education Organic Chemistry Ether 02 engineering and technology Tetramethylethylenediamine 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences Catalysis chemistry.chemical_compound Electron transfer Polymer chemistry Thiol Amine gas treating 0210 nano-technology |
| Zdroj: | The Journal of Organic Chemistry. 83:2912-2919 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | The effect of amines on the kinetics and efficacy of radical-mediated thiol-ene coupling (TEC) reactions was investigated. By varying the thiol reactant and amine additive, it was shown that amines retard thiyl radical-mediated reactions when the amine is adequately basic enough to deprotonate the thiol affording the thiolate anion, e.g., when the weakly basic amine tetramethylethylenediamine was incorporated in the TEC reaction between butyl 2-mercaptoacetate and an allyl ether at 5 mol %, the final conversion was reduced from quantitative to |
| Databáze: | OpenAIRE |
| Externí odkaz: |
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