Halogenation of 4-aroyl(arylsulfonyl)imino-2,6-diisopropylcyclohexa-2,5-dien-1-ones gave 4-aroyl(arylsulfonyl)imino-3-halo-2,6-diisopropylcyclohexa-2,5-dien- -1-ones and 4-aroyl(arylsulfonyl)imino-3,5,6-trihalo-2,6-diisopropylcyclobex-2-en-1-ones. The latter were formed as mixtures of two stereoisomers, and the isopropyl group on the sp(3)-hybridized carbon atom in one stereoisomer occupies axial position, which is untypical of such compounds. Halogenation of 4-aroyl(arylsulfonyl)oxyimino-2,6-diisopropylcyclohexa-2,5-dien-1-ones leads to the formation of the corresponding addition products with traditional trans-diaxial arrangement of the halogen atoms.