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The Strong β−CF3 Shielding Effect in Hexafluoroisopropanol and 100 Other Organic Solvents Revisited with 17O NMR Spectroscopy
ChemCatChem ( IF 3.8 ) Pub Date : 2018-02-23 , DOI: 10.1002/cctc.201701721
Annika Bernhardt 1 , Harald Kelm 1 , Frederic W Patureau 1
Affiliation  

An 17O NMR spectroscopy survey of more than 100 ubiquitous organic solvents and compounds, including some typical oxofluorinated solvents such as hexafluoroisopropanol, trifluoroethanol, trifluoroacetic acid, and others, is presented with D2O as a reference. A strong alternating α,β−CF3‐substituent chemical shift effect was thus observed. This alternating deshielding–shielding effect is suspected to have a role in the exceptional properties of these oxofluorinated solvents, notably in oxidative cross‐coupling reactions.

中文翻译:


用 17O NMR 光谱重新审视六氟异丙醇和 100 种其他有机溶剂中的强 β−CF3 屏蔽效应



以 D 2 O 作为参考,对 100 多种普遍存在的有机溶剂和化合物(包括一些典型的氟代溶剂,如六氟异丙醇、三氟乙醇、三氟乙酸等)进行了17 O NMR 谱调查。因此观察到强烈的交替α,β-CF 3取代基化学位移效应。这种交替的去屏蔽-屏蔽效应被怀疑在这些氟代溶剂的特殊性质中发挥着作用,特别是在氧化交叉偶联反应中。
更新日期:2018-02-23
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