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Reaction of 2,3-epoxyoctafluorobutane with 2-aminobenzenethiol

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Abstract

The reaction of 2,3-epoxyoctafluorobutane with 2-aminobenzenethiol in N,N-dimethylacetamide gave 3-(2-aminophenylsulfanyl)-1,1,1,3,4,4,4-heptafluorobutane-2,2-diol. In the reaction of the same compounds in dioxane, 2,3-bis(trifluoromethyl)-3,4-dihydro-2H-1,4-benzothiazin-2-ol was formed as a result of primary attack by the amino group in 2-aminobenzenethiol on the epoxy ring. The same product was obtained by treatment with 2-aminobenzenethiol of 2,3-bis(trifluoromethyl)-2H-1,4-benzoxazin-2-ol which was synthesized from 2,3-epoxyoctafluorobutane and 2-aminophenol.

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Authors and Affiliations

  1. Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, ul. S. Kovalevskoi 20, Yekaterinburg, 620219, Russia

    L. V. Saloutina, A. Ya. Zapevalov, V. I. Saloutin, M. I. Kodess, V. E. Kirichenko, M. G. Pervova & O. N. Chupakhin

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  1. L. V. Saloutina
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  2. A. Ya. Zapevalov
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  3. V. I. Saloutin
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  4. M. I. Kodess
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  5. V. E. Kirichenko
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  6. M. G. Pervova
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  7. O. N. Chupakhin
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Additional information

Original Russian Text © L.V. Saloutina, A.Ya. Zapevalov, V.I. Saloutin, M.I. Kodess, V.E. Kirichenko, M.G. Pervova, O.N. Chupakhin, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 9, pp. 1328–1332.

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Saloutina, L.V., Zapevalov, A.Y., Saloutin, V.I. et al. Reaction of 2,3-epoxyoctafluorobutane with 2-aminobenzenethiol. Russ J Org Chem 42, 1307–1312 (2006). https://doi.org/10.1134/S1070428006090090

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  • DOI: https://doi.org/10.1134/S1070428006090090

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