Reactions of cyclopropanes with potassium dihaloiodates

Reactions of potassium dihaloiodates with arylcyclopropanes and polycyclic compounds containing a cyclopropane fragment characterized by different degrees of strain lead to formation of mixed 1,3-halogenation products. If iodohalogenation should give rise to products having a iodine atom in the benzylic position, 1,3-dichloro or 1,3-dibromo derivatives are formed. Iodohalogenation of exo-tricyclo[3.2.1.02,4]octane is stereoselective and is accompanied by Wagner-Meerwein rearrangement.