Activated Iodosylbenzene Monomer as an Ozone Equivalent: Oxidative Cleavage of Carbon−Carbon Double Bonds in the Presence of Water

Reported here for the first time are the developments of an efficient method for oxidative cleavage of carbon−carbon double bonds yielding carbonyl compounds by using aryl-λ 3 -iodanes, which involve a combination of iodosylbenzene and HBF 4 in the presence of water. The method serves as a safety alternative to ozonolysis. The oxidative cleavage of olefins probably involves the hitherto unknown direct vicinal dihydroxylations of double bonds with aryl-λ 3 -iodanes and the subsequent oxidative glycol fissions. Cyclic (cyclopentenes, cyclohexenes, etc.) and acyclic olefins are cleaved smoothly under our conditions. In the reaction of electron-deficient styrenes such as m -nitrostyrene, intermediate formation of the corresponding epoxide was detected. A variety of aryloxiranes also undergo an oxidative cleavage of the epoxide rings under our conditions, and aromatic aldehydes were obtained in good yields