ChemInform Abstract: Iron(III)-Induced Cleavage of Cyclic Allylic Hydroperoxides to Dicarbonyl Compounds Under Aprotic Conditions.

ChemInform Abstract

Treatment of the pinene hydroperoxide (I) with iron trichloride etherate in dichloromethane leads to the formation of the keto aldehyde (II). Similarly, the unsaturated steroidal hydroperoxide (III) is cleaved to give the isomeric alcohols (IV) via recyclization. When the hydroperoxide (V) is treated with an iron(III) phenanthroline complex, the keto aldehyde (VI) is obtained as the main product. The cleavage of hydroperoxides and a stannyl peroxide is also investigated under various reaction conditions.