Abstract The specifically designed reagent, 4-t Butyl iodoxybenzene (1)-soluble in hot, benzene, chlorobenzene and nitrobenzene-cleaves a range of π bonds to carbonyl compounds in 50–75% isolated yields. In every case, the reagent 1 is transformed to 4-t butyl iodobenzene (2) in 90–97% yields, which can be recycled.