Oxidations of alkenes with hypervalent iodine reagents: an alternative ozonolysis of phenyl substituted alkenes and allylic oxidation of unsubstituted cyclic alkenes

Unsaturated C=C double bonds with a phenyl substituent can be cleaved with iodylbenzene and iodosylbenzene to give carbonyl compounds. It is believed that the reactions occur via a radical pathway. The allylic oxidation of cyclic alkenes lacking a phenyl substituent was achieved in acetonitrile/water mixture (3:1) also using iodylbenzene and iodosylbenzene. (C) 2014 Elsevier Ltd. All rights reserved.