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200517.fm Page 49 Friday, March 18, 2005 2:52 PM
2005
Oxidation
O 0212
17- 047
Synthesis, Characterization, and Reaction of Crown Ether Complexes of
Aqua(hydroxy)(aryl)iodonium Ions. — The synthesis and characterization of a
crown ether complex of aqua(hydroxy)(phenyl)iodonium tosylate (HPIT) is presented.
This complex is surprisingly stable in solid state and in solution and serves as an excellent oxidant in aqueous solutions. Thus, sulfide (I), phenols (III), (V) as well as styrene
derivatives (VII) and (IX) are smoothly oxidized. In contrast, the reaction with stannane
(XIII) and trifluoroborate (XVI) proceeds with Sn—I and B—I exchange, resp., to give
the iodosylbenzene derivatives (XV) and (XVII) as crown ether complexes. —
(OCHIAI*, M.; MIYAMOTO, K.; YOKOTA, Y.; SUEFUJI, T.; SHIRO, M.; Angew.
Chem., Int. Ed. 44 (2005) 1, 75-78; Fac. Pharm. Sci., Univ. Tokushima, Sho,
Tokushima 770, Japan; Eng.) — Mischke
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