Abstract
Lewis acid-activated iodosylbenzene reacts readily with a variety of organosilicon and tin compounds to produce hypervalent organoiodine (III) species. Allyl- and vinyliodine (III) compounds act as highly reactive species equivalent to allyl and vinyl cations. Tandem Michael-carbene insertion reaction of alkynyliodine (III) compounds offers an efficient procedure for the synthesis of highly functionalized cyclopentenes. Intramolecular hypervalent Sn-O interaction makes possible the fixation of 6-membered carbocycles to the 1, 3-diaxial conformer and the highly stereoselective osmylation of olefins. Synthesis of functionalized olefins utilizing an oxidative 1, 4-fragmentation of γ-stannyl alcohols and a β-elimination of silyl and stannyl organosulfur compounds is also described.
