- Reactions of epoxides derived from internal perfluoroolefins with o-phenylenediamine and 2-aminophenol
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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. Pleiades Publishing, Inc., 2006.
- Saloutina,Zapevalov,Saloutin,Kodess,Kirichenko,Pervova,Chupakhin
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p. 558 - 566
(2007/10/03)
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- Synthesis of 2,3-bis(perfluoroalkyl)quinoxalines and 2,3- bis(perfluoroalkyl)-1,4-benzoxazines from oxides of internal perfluoroolefins
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The reactions of oxides of internal trans-, cis-perfluoroolefins with o-phenylenediamine and 2-aminophenol in dioxane gave 2,3-bis(perfluoroalkyl) quinoxalines and 2,3-bis(perfluoroalkyl)-2H-1,4-benzoxazin-2-ols respectively in yields of 23-67%. When N,N-dimethylacetamide was used as a solvent an anionic isomerization of the oxides into ketones, which further yielded 2-(perfluoroalkyl)benzimidazoles in the case of o-phenylenediamine and 2-hydroxy-N-perfluoroalkanoylanilines in the case of 2-aminophenol, became the main path of these reactions. Unusual cyclization resulting in 2-pentafluoroethyl-2-pentafluoropropanoylbenzoxazolidine occurs on interaction between dodecafluoro-3,4-epoxyhexane and 2-aminophenol in N,N-dimethylacetamide.
- Saloutina, Lyudmila V.,Zapevalov, Aleksandr Ya.,Saloutin, Victor I.,Kodess, Mikhail I.,Kirichenko, Valentina E.,Pervova, Marina G.,Chupakhin, Oleg N.
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p. 976 - 983
(2007/10/03)
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- Reactions Involving Fluoride Ion. Part 30. Preparation and Reactions of Epoxides Derived from Perfluoroalkyl Substituted Alkenes
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Reactions of alkenes that are oligomers of tetrafluoroethene or hexafluorocyclobutene with sodium hypochlorite give epoxides which show remarkable overall stability.Ring-opening reactions, induced by fluoride ion, yield alkenes, ketones, and acid fluorides.
- Bryce, Martin R.,Chambers, Richard D.,Kirk, Julian R.
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p. 1391 - 1395
(2007/10/02)
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