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4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N(2) atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4-(p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N—Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5-polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5-polyfluoroalkyl-2H-[1,2,3]triazoles.

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Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, Kiev, 02094

    Yu. P. Bandera, O. S. Kanishchev, V. M. Timoshenko, S. A. But, A. M. Nesterenko & Yu. G. Shermolovich

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  1. Yu. P. Bandera
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  2. O. S. Kanishchev
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  3. V. M. Timoshenko
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  4. S. A. But
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  5. A. M. Nesterenko
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  6. Yu. G. Shermolovich
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Correspondence to Yu. G. Shermolovich.

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__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1342–1352, September, 2007.

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Bandera, Y.P., Kanishchev, O.S., Timoshenko, V.M. et al. 4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles. Chem Heterocycl Comp 43, 1138–1147 (2007). https://doi.org/10.1007/s10593-007-0175-x

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  • DOI: https://doi.org/10.1007/s10593-007-0175-x

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