Synthesis of 2,3-bis(perfluoroalkyl)quinoxalines and 2,3-bis(perfluoroalkyl)-1,4-benzoxazines from oxides of internal perfluoroolefins

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• 作者：Saloutina ; Lyudmila V. ; Zapevalov ; Aleksandr Ya. ; Saloutin ; Victor I. ; Kodess ; Mikhail I. ; et. al.
• 关键词：Oxides of internal perfluoroolefins ; O-phenylenediamine ; 2-Aminophenol ; 2 ; 3-Bis(perfluoroalkyl)quinoxalines ; 2 ; 3-Bis(perfluoroalkyl)-1 ; 4-benzoxazines ; 2-(Perfluoroalkyl)benzimidazoles ; 2-Hydroxy-N-perfluoroalkanoylanilines
• 刊名：Journal of Fluorine Chemistry
• 出版年：2005
• 出版时间：June, 2005
• 年：2005
• 卷：126
• 期：6
• 页码：976-983
• 全文大小：291 K

文摘

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.