Reactivity and Synthetic Utility of 1-(Arenesulfonyloxy)benziodoxolones.
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.
Muraki
Takahito
T
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.
Togo
Hideo
H
Yokoyama
Masataka
M