383-08-4Relevant academic research and scientific papers
Reactions of perfluoro(2,3-epoxy-2-methylpentane) with o-phenylenediamine and ethylenediamine
Filyakova,Zapevalov, A. Ya.,Kodess,Slepukhin,Saloutin
, p. 350 - 355 (2013/07/26)
Perfluoro(2,3-epoxy-2-methylpentane) reacted with o-phenylenediamine and ethylenediamine via cleavage of the C-C bond to produce 2,2,3,3,3-pentafluoro-N- [2-(2,2,2-trifluoro-1-trifluoromethylethylamino)-phenyl]propanamide and 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)ethyl] -propanamide, respectively. Presumably, these compounds are formed as a result of rearrangement of intermediate ketone generated by intramolecular haloform-type reaction. According to the NMR and X-ray diffraction data, 2,2,3,3,3-pentafluoro-N-[2-(2,2,2-trifluoro-1-trifluoromethylethylamino)phenyl] propanamide in crystal exists as Z conformer with respect to the amide C-N bond.
Reactions of epoxides derived from internal perfluoroolefins with o-phenylenediamine and 2-aminophenol
Saloutina,Zapevalov,Saloutin,Kodess,Kirichenko,Pervova,Chupakhin
, p. 558 - 566 (2007/10/03)
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.
Synthesis of 2,3-bis(perfluoroalkyl)quinoxalines and 2,3- bis(perfluoroalkyl)-1,4-benzoxazines from oxides of internal perfluoroolefins
Saloutina, Lyudmila V.,Zapevalov, Aleksandr Ya.,Saloutin, Victor I.,Kodess, Mikhail I.,Kirichenko, Valentina E.,Pervova, Marina G.,Chupakhin, Oleg N.
, p. 976 - 983 (2007/10/03)
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.
