title: Preparation and chemistry of phosphoranyl-derived iodanes.
abstract: The preparation and chemistry of novel phosphoranyl-derived lambda(3)-iodanes is reported. The phosphoranyl-derived phenyliodonium sulfonates were prepared in good yields by the reaction of stabilized phosphonium ylides [1-triphenylphosphoranylidene-2-propanone, methyl(triphenylphosphoranylidene)acetate, (triphenylphosphoranylidene)acetaldehyde, and (triphenylphosphoranylidene)acetonitrile] with the pyridinium complex of iodobenzene ditriflate or with [hydroxy(tosyloxy)iodo]benzene under mild conditions. These compounds represent a potentially useful class of reagents that combine in one molecule synthetic advantages of a phosphonium ylide and an iodonium salt. Specifically, phosphorane-derived phenyliodonium tosylates can react with soft nucleophiles, such as iodide, bromide, benzenesulfinate, and thiophenolate anions, with a selective formation of the respective alpha-functionalized phosphonium ylides, which can be further converted to alkenes by the Wittig reaction with benzaldehyde. The phosphoranyl-derived benziodoxoles can be prepared by the reaction of 1-acetoxybenziodoxole with stabilized phosphonium ylides. An unusual ligand exchange on the iodine(III) center resulting in the substitution of a carbon ligand with an oxygen ligand was observed in the reaction of these compounds with strong acids.
authors.affiliation: Department of Chemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, USA. vzhdanki@d.umn.edu
authors.forename: Viktor V
authors.initials: VV
authors.lastname: Zhdankin
authors.forename: Olena
authors.initials: O
authors.lastname: Maydanovych
authors.forename: Jon
authors.initials: J
authors.lastname: Herschbach
authors.forename: Jessica
authors.initials: J
authors.lastname: Bruno
authors.forename: Elena D
authors.initials: ED
authors.lastname: Matveeva
authors.forename: Nikolai S
authors.initials: NS
authors.lastname: Zefirov