Abstract: 2-Iodo-4,4′-dinitrodiphenyl amine 3 and 2,2′-diiodo-4,4′- dinitrodiphenyl amine 6 were prepared by direct iodination with SbCl₅/I₂, from 4,4′-dinitrodiphenyl amine. Cyclization of 3 and 6 with K₂S₂O₈/H₂SO₄ results in 4 and 7, respectively. 4 was reduced and acetylated to give 5. Reduction of 7 obtained 8. 8 was convened into 9,10,11, respectively, by diazotization and halogenation. compounds 4,5 and 7-11 are new 9-imine-dibenzocycloiodonium salts. Their structures were confirmed by IR, NMRand MS.