Synthesis of Perfluoro- and 2-Trifluoromethylpentafluorodihydrofurans and Their Epoxy Derivatives
摘要:
Perfluorotetrahydrofuran-2-carboxylic acid was converted through a series of transformations into perfluoro-2,3-dihydrofuran and perfluoro-2,5-dihydrofuran; likewise, from (2-perfluorotetrahydrofuryl)difluoroacetic acid 2-trifluoromethylpentafluoro-2,3-dihydrofuran was obtained. Perfluoro-2,3-dihydrofuran and 2-trifluoromethylpentafluoro-2,3-dihydrofuran underwent isomerization into perfluoro-2,5-dihydrofuran and 2-trifluoromethylpentafluoro-2,5-dihydrofuran by the action of cesium fluoride. Treatment of perfluoro-2,5-dihydrofuran with SbF5 resulted in ring opening and formation of cis-perfluoro-2-butenoyl fluoride, while 2-trifluoromethylpentafluoro-2,3-dihydrofuran was converted into 2-trifluoromethylpentafluoro-2,5-dihydrofuran under the same conditions. Perfluoro-3,4-epoxytetrahydrofuran and 2-trifluoromethyl-3,4-epoxypenta-fluorotetrahydrofuran containing fused oxirane and tetrahydrofuran rings were synthesized by reactions of perfluoro-2,5-dihydrofuran and 2-trifluoromethylpentafluoro-2,5-dihydrofuran, respectively, with sodium hypochlorite.
Synthesis of Perfluoro- and 2-Trifluoromethylpentafluorodihydrofurans and Their Epoxy Derivatives
摘要:
Perfluorotetrahydrofuran-2-carboxylic acid was converted through a series of transformations into perfluoro-2,3-dihydrofuran and perfluoro-2,5-dihydrofuran; likewise, from (2-perfluorotetrahydrofuryl)difluoroacetic acid 2-trifluoromethylpentafluoro-2,3-dihydrofuran was obtained. Perfluoro-2,3-dihydrofuran and 2-trifluoromethylpentafluoro-2,3-dihydrofuran underwent isomerization into perfluoro-2,5-dihydrofuran and 2-trifluoromethylpentafluoro-2,5-dihydrofuran by the action of cesium fluoride. Treatment of perfluoro-2,5-dihydrofuran with SbF5 resulted in ring opening and formation of cis-perfluoro-2-butenoyl fluoride, while 2-trifluoromethylpentafluoro-2,3-dihydrofuran was converted into 2-trifluoromethylpentafluoro-2,5-dihydrofuran under the same conditions. Perfluoro-3,4-epoxytetrahydrofuran and 2-trifluoromethyl-3,4-epoxypenta-fluorotetrahydrofuran containing fused oxirane and tetrahydrofuran rings were synthesized by reactions of perfluoro-2,5-dihydrofuran and 2-trifluoromethylpentafluoro-2,5-dihydrofuran, respectively, with sodium hypochlorite.
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申请人:ASAHI GLASS COMPANY LTD.
公开号:EP1548014B1
公开(公告)日:2009-04-22
Synthesis of Perfluoro- and 2-Trifluoromethylpentafluorodihydrofurans and Their Epoxy Derivatives
作者:T. I. Filyakova、M. I. Kodess、A. Ya. Zapevalov、V. I. Saloutin
DOI:10.1023/b:rujo.0000003194.13428.68
日期:2003.7
Perfluorotetrahydrofuran-2-carboxylic acid was converted through a series of transformations into perfluoro-2,3-dihydrofuran and perfluoro-2,5-dihydrofuran; likewise, from (2-perfluorotetrahydrofuryl)difluoroacetic acid 2-trifluoromethylpentafluoro-2,3-dihydrofuran was obtained. Perfluoro-2,3-dihydrofuran and 2-trifluoromethylpentafluoro-2,3-dihydrofuran underwent isomerization into perfluoro-2,5-dihydrofuran and 2-trifluoromethylpentafluoro-2,5-dihydrofuran by the action of cesium fluoride. Treatment of perfluoro-2,5-dihydrofuran with SbF5 resulted in ring opening and formation of cis-perfluoro-2-butenoyl fluoride, while 2-trifluoromethylpentafluoro-2,3-dihydrofuran was converted into 2-trifluoromethylpentafluoro-2,5-dihydrofuran under the same conditions. Perfluoro-3,4-epoxytetrahydrofuran and 2-trifluoromethyl-3,4-epoxypenta-fluorotetrahydrofuran containing fused oxirane and tetrahydrofuran rings were synthesized by reactions of perfluoro-2,5-dihydrofuran and 2-trifluoromethylpentafluoro-2,5-dihydrofuran, respectively, with sodium hypochlorite.