Synthesis of fluorine containing glycolurils and oxazolines from oxides of internal perfluoroolefins

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• 作者：Lyudmila V. Saloutina ; Aleks ; r Ya. Zapevalov ; Victor I. Saloutin ; Pavel A. Slepukhin ; Mikhail I. Kodess ; Oleg N. Chupakhin
• 关键词：Oxides of internal perfluoroolefins ; Urea ; 1 ; 5-Bis(perfluoroalkyl)tetraazabicyclo[3.3.0]octane-3 ; 7-diones ; 2-Amino-5-fluoro-4 ; 5-bis(perfluoroalkyl)-4 ; 5-dihydrooxazol-4-ols ; 4 ; 5-Dihydroxy-4 ; 5-bis(perfluoroalkyl)imidazolidine-2-ones
• 刊名：Journal of Fluorine Chemistry
• 出版年：2009
• 出版时间：October 2009
• 年：2009
• 卷：130
• 期：10
• 页码：853-860
• 全文大小：505 K

文摘

The reaction of oxides of internal perfluoroolefins 1–3 with urea gave two kinds of novel fluorine containing N-heterocyclic compounds depending on the solvent nature: 1,5-bis(perfluoroalkyl)tetraazabicyclo[3.3.0]octane-3,7-diones 4a–c and 2-amino-5-fluoro-4,5-bis(perfluoroalkyl)-4,5-dihydrooxazol-4-ols 7a–d. Use of polar dimethylsulfoxide, N,N-dimethylacetamide and acetonitrile afforded glycolurils 4a–c in moderate yields. In dioxane, unexpected cyclization occurred resulting in oxazolines 7a–d in high yields. A similar reaction of oxiranes 2, 3 with urea in aqueous dioxane gave mixtures of 4,5-dihydroxy-4,5-bis(perfluoroalkyl)imidazolidine-2-ones 9b, c, glycolurils 4b, c and oxazolines 7b–d. The molecular structure of trans-isomers of oxazoline 7b and imidazolidine 9b has been established by X-ray crystallography.