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Synthesis and transformations of bis(polychloroethylideneaminosulfonyl)- and bis(polychloroethylideneaminosulfonyl)-substituted derivatives of biphenyl, diphenyl oxide, and diphenylmethane

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Abstract

Reactions of N,N,N′,N′-tetrachlorobiphenyl-4,4′-disulfonamide, 4,4′-methylenebis(N,N-dichlorobenzenesulfonamide), and 4,4′-oxybis(N,N-dichlorobenzenesulfonamide) with 1,2-dichloroethylene and trichloroethylene open convenient synthetic approach to highly electrophilic bissulfony limines of dichloroacetic aldehyde and chloral: N,N′-bis(polychloroethylidene)biphenyl-4,4′-disulfonamides, 4,4′-methylenebis[N-(polychloroethylidene)benzenesulfonamides] and 4,4′-oxybis[N-(polychloroethylidene)benzenesulfonamides]. The synthetic opportunities of the bisazomethines obtained were demonstrated by examples of their reactions with water, methanol, chloroacetamide, and toluene where products of O-, N-nucleophiles addition to the azomethine bond and products of C-amidoalkylation of aromatic compound with imines were formed.

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Authors and Affiliations

  1. Faworsky Irkutsk Institute of Chemistry, Siberian Division, Russian Academy of Sciences, Irkutsk, 664033, Russia

    I. B. Rosentsveig, I. V. Ushakova, A. N. Mirskova & G. G. Levkovskaya

Authors
  1. I. B. Rosentsveig
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  2. I. V. Ushakova
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  3. A. N. Mirskova
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  4. G. G. Levkovskaya
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Correspondence to I. B. Rosentsveig.

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Original Russian Text © I.B. Rosentsveig, I.V. Ushakova, A.N. Mirskova, G.G. Levkovskaya, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 2, pp. 227–233.

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Rosentsveig, I.B., Ushakova, I.V., Mirskova, A.N. et al. Synthesis and transformations of bis(polychloroethylideneaminosulfonyl)- and bis(polychloroethylideneaminosulfonyl)-substituted derivatives of biphenyl, diphenyl oxide, and diphenylmethane. Russ J Org Chem 44, 218–224 (2008). https://doi.org/10.1134/S1070428008020061

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  • DOI: https://doi.org/10.1134/S1070428008020061

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