Reactions of iodine oxide with alkenes

Abstract

The reaction of solvated iodine oxide, prepared by ozonising a solution of iodine in acetic anhydride, with alkenes has been examined. The reaction is regiospecific and leads to vic-iodo-acetates, iodohydrins, and iodo-ketones. In some cases di- and tri-acetates and 2,2′-di-iodo-ethers are formed. The products from norbornene are similar to those formed with thallium(I) acetate and iodine. The mode of formation of the products is discussed and the effect of non-polar solvents is investigated.