Reactions of N-substituted 2,6(3,5)-dialkyl-1,4-benzoquinone imines with arenesulfinic acids |
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| Authors: | A P Avdeenko S A Konovalova D A Roman’kov K S Burmistrov V M Nichvoloda O V Shishkin R I Zubatyuk G V Palamarchuk |
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| Institution: | (1) Donbass State Machine-Building Academy, ul. Shkadinova 72, Kramatorsk, 84313, Ukraine;(2) Ukrainian State University of Chemical Technology, Dnepropetrovsk, Ukraine;(3) Institute of Single Crystals, National Academy of Sciences of Ukraine, Kharkov, Ukraine |
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| Abstract: | The regioselectivity in the reactions of N-arylsulfonyl-2,6-dialkyl-1,4-benzoquinone imines with arenesulfinic acids (1,6-, 6,1-, or 6,3-addition) is determined by steric factor, while in the reactions of N-aroyl-1,4-benzoquinone imines electronic effect of substituents in the quinoid ring is crucial. The reactions of N-arylsulfonyl-3,5-dimethyl-1,4-benzoquinone imines with arenesulfinic acids follow mainly the 1,4-addition pattern. N-(N-Arylsulfonylbenzimidoyl)-1,4-benzoquinone imines are capable of reacting in a way similar to both N-arylsulfonyl and N-aroyl derivatives. |
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