Halogenation of N-substituted p-quinone monoimines and p-quinone monooxime esters: VII. Halogenation of 4-aroyl(arylsulfonyl)imino- and 4-aroyl(arylsulfonyl)-oxyimino-2,6-diisopropylcyclohexa-2,5-dien-1-ones |
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| Authors: | A. P. Avdeenko V. V. Pirozhenko O. V. Shishkin S. V. Shishkina S. A. Konovalova O. N. Ludchenko |
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| Affiliation: | (1) Donbass State Machine-Building Academy, ul. Shkadinova 72, Kramatorsk, 84313, Ukraine;(2) Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, Ukraine;(3) Institute of Single Crystals, National Academy of Sciences of Ukraine, Khar’kov, Ukraine |
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| Abstract: | 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-diisopropylcyclohex-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. |
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