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Reactivity of Hydroxy‐ and Aquo(hydroxy)‐λ 3 ‐iodane–Crown Ether Complexes
Author(s) -
Miyamoto Kazunori,
Yokota Yukie,
Suefuji Takashi,
Yamaguchi Kentaro,
Ozawa Tomoyuki,
Ochiai Masahito
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201304961
Subject(s) - chemistry , acetonitrile , dichloromethane , reagent , crown ether , oxidizing agent , reactivity (psychology) , enol , aqueous solution , organic chemistry , medicinal chemistry , silylation , aryl , methanol , alkyl , polymer chemistry , catalysis , solvent , medicine , ion , alternative medicine , pathology
We have designed a series of hydroxy(aryl)‐λ 3 ‐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‐λ 3 ‐iodane–[18]crown‐6 complexes serve as efficient progenitors for the synthesis of diaryl‐, vinyl‐, and alkynyl‐λ 3 ‐iodanes in water. Other less polar organic solvents, such as methanol, acetonitrile, and dichloromethane, are also usable in some cases.