Halogenation of N-substituted para-quinone monoimines and para-quinone monoximes ethers: IX. Halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone monoimines and their reduced forms |
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| Authors: | A P Avdeenko S A Konovalova O N Ludchenko G V Palamarchuk and O V Shishkin |
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| Institution: | (1) Institute for Biotechnology and Bioengineering, Centre of Biological Engineering, Universidade do Minho, Campus de Gualtar, 4710-057 Braga, Portugal;(2) School of Biological Sciences, Biomedical Sciences Building, University of Southampton, Bassett Crescent East, Southampton, SO16 7PX, UK |
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| Abstract: | At the halogenation of N-aroyl-2,6(3,5)-dimethyl-1,4-benzoquinone imines we found the halogenation of methyl groups to occur. The bromination of N-aroyl-2,6-dimethyl-1,4-benzoquinone imines yielded 3,6-dibromo-2,6-dimethyl-5-aroyloxycyclohex-2-ene-1,4-diones due to the
strong acceptor property of the ArCO group and high redox potentials of N-aroyl derivatives. In the chlorination of N-aroyl-3,5-dimethyl-1,4-benzoquinone imines the chlorine addition to the C=C bond of the quinoid ring proceeded both by the
trans- and syn-scheme. |
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