Reactions of epoxides derived from internal perfluoroolefins with o-phenylenediamine and 2-aminophenol |
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Authors: | 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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Affiliation: | (1) Institute of Organic Synthesis, Ural Division, Russian Academy of Sciences, ul. S. Kovalevskoi 20, Yekaterinburg, 620219, Russia |
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Abstract: | The reactions of epoxy derivatives of internal perfluoroolefins with o-phenylenediamine and 2-aminophenol in dioxane gave 23–67% of the corresponding 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-2H-1,4-benzoxazin-2-ols, respectively. When N,N-dimethylacetamide was used as a solvent, the main reaction pathway was anionic isomerization of epoxides into ketones which were then converted into 2-perfluoroalkylbenzimidazoles (in the reactions with o-phenylenediamine) or 2-hydroxy-N-perfluoroalkanoylanilines (in the reactions with 2-aminophenol). The reaction of 3,4-epoxydodecafluorohexane with 2-aminophenol in N,N-dimethylacetamide was accompanied by unusual cyclization to afford 2-pentafluoropropanoyl-2-pentafluoroethyl-1,3-benzoxazolidine. |
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