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Synthesis of 2-methyl-N-(2,2,2-trichloroethylidene)- and 2-methyl-N-(2,2,2-trichloroethyl)benzenesulfonamides from N,N-dichloro-2-methylbenzenesulfonamide and trichloroethylene

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Abstract

The reaction of N,N-dichloro-2-methylbenzenesulfonamide with trichloroethylene gave a new representative of highly electrophilic N-sulfonyl polyhaloaldehyde imines, 2-methyl-N-(2,2,2-trichloroethylidene) benzenesulfonamide. High reactivity of the product was demonstrated in the addition of water and 2-methylbenzenesulfonamide and reactions with benzene, toluene, anisole, thiophene, and 2-chlorothiophene. N,N-Dichlorobenzenesulfonamides and N,N-dichlorotrifluoromethanesulfonamide failed to react with 1,1,3,3,4,4-hexachlorobut-1-ene and 1,1,2,3,4-pentachlorobuta-1,3-diene under the conditions ensuring formation of N-(2,2,2-trichloroethylidene)arenesulfonamides from N,N-dichloroarenesulfonamides and trichloroethylene.

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Correspondence to Yu. A. Aizina.

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Original Russian Text © Yu.A. Aizina, I.B. Rozentsveig, S.K. Petkevich, V.I. Potkin, G.G. Levkovskaya, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 3, pp. 366–371.

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Aizina, Y.A., Rozentsveig, I.B., Petkevich, S.K. et al. Synthesis of 2-methyl-N-(2,2,2-trichloroethylidene)- and 2-methyl-N-(2,2,2-trichloroethyl)benzenesulfonamides from N,N-dichloro-2-methylbenzenesulfonamide and trichloroethylene. Russ J Org Chem 50, 355–360 (2014). https://doi.org/10.1134/S1070428014030099

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