title: Reactivity and Synthetic Utility of 1-(Arenesulfonyloxy)benziodoxolones.
abstract: The reactivity and synthetic use of 1-(arenesulfonyloxy)benziodoxolones were studied. In the presence of iodine, 1-(arenesulfonyloxy)benziodoxolones iodinated various aromatics to give iodoarenes in moderate to good yields. In particular, 1-(p-chlorobenzenesulfonyloxy)benziodoxolone showed the best reactivity. Using a halide salt such as lithium bromide or lithium chloride instead of iodine, the corresponding aryl bromides and chlorides were also obtained in good yields. In the absence of aromatics, 1-(arenesulfonyloxy)benziodoxolones gave rise to desulfonyloxyiodination reactions to give the corresponding aryl iodides via electrophilic ipso substitution on the aromatic rings. Furthermore, the 1-(p-toluenesulfonyloxy)benziodoxolone/iodine system iodotosyloxylated alkynes in good yields. These reactions proceeded via the formation of arenesulfonyl hypoiodites.
authors.affiliation: Graduate School of Science and Technology, and Department of Chemistry, Faculty of Science, Chiba University, Yayoi cho 1-33, Inage-ku, Chiba 263-8522, Japan.
authors.forename: Takahito
authors.initials: T
authors.lastname: Muraki
authors.forename: Hideo
authors.initials: H
authors.lastname: Togo
authors.forename: Masataka
authors.initials: M
authors.lastname: Yokoyama