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Reaction of N-substituted 2,5-dialkyl-1,4-benzoquinone imines with arenesulfinic acids

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Abstract

Reactions of N-aroyl-, N-arylsulfonyl-, and N-(N-arylsulfonylbenzimidoyl)-2,5-dialkyl-1,4-benzoquinone imines with sodium arenesulfinates in acetic acid gave the corresponding 1,4-, 6,1-, and 1,6-addition products. Variation of the size and donor power of substituents in positions 2 and 5 of the quinoid ring almost does not affect the ratio of the addition products, which is determined mainly by the nature of substituent on the nitrogen atom.

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Correspondence to A. P. Avdeenko.

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Original Russian Text © A.P. Avdeenko, S.A. Konovalova, D.A. Roman’kov, O.N. Ludchenko, I.L. Marchenko, 2009, published in Zhurnal Organicheskoi Khimii, 2009, Vol. 45, No. 3, pp. 395–405.

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Avdeenko, A.P., Konovalova, S.A., Roman’kov, D.A. et al. Reaction of N-substituted 2,5-dialkyl-1,4-benzoquinone imines with arenesulfinic acids. Russ J Org Chem 45, 383–393 (2009). https://doi.org/10.1134/S1070428009030063

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  • DOI: https://doi.org/10.1134/S1070428009030063

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