Novel features of iron-mediated radical reactions: an unusual mode of silyloxycyclopropane fission, and a new method for radical chain termination using CH2I2

Fe(NO3)3 mediated radical reactions of silyloxycyclopropanes derived from a range of bicyclic ketones are described, and include examples that undergo an unexpected regiochemical mode of cyclopropane cleavage. The inclusion of CH2I2 in such reactions allows the synthesis of iodinated products.