Reactivity of Hydroxy‐ and Aquo(hydroxy)‐λ3‐iodane–Crown Ether Complexes |
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| Authors: | Prof?Dr Kazunori Miyamoto Dr Yukie Yokota Dr Takashi Suefuji Prof?Dr Kentaro Yamaguchi Dr Tomoyuki Ozawa Prof?Dr Masahito Ochiai |
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| Affiliation: | 1. Graduate School of Pharmaceutical Sciences, University of Tokushima, 1‐78 Shomachi, Tokushima 770‐8505 (Japan);2. Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314–1 Shido, Sanuki, Kagawa 769–2193 (Japan);3. Chemical Research Laboratories, Nissan Chemical Industries Ltd. 722–1 Tsuboi‐cho, Funabashi, Chiba 274–8507 (Japan) |
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| Abstract: | We have designed a series of hydroxy(aryl)‐λ3‐iodane–18]crown‐6 complexes, prepared from the corresponding iodosylbenzene derivatives and superacids in the presence of 18]crown‐6, and have investigated their reactivities in aqueous media. These activated iodosylbenzene monomers are all non‐hygroscopic shelf‐storable reagents, but they maintain high oxidizing ability in water. The complexes are effective for the oxidation of phenols, sulfides, olefins, silyl enol ethers, and alkyl(trifluoro)borates under mild conditions. Furthermore, hydroxy‐λ3‐iodane–18]crown‐6 complexes serve as efficient progenitors for the synthesis of diaryl‐, vinyl‐, and alkynyl‐λ3‐iodanes in water. Other less polar organic solvents, such as methanol, acetonitrile, and dichloromethane, are also usable in some cases. |
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| Keywords: | crown ethers hypervalent compounds iodine oxidation supramolecules |
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