Difluorocarbene chemistry: synthesis of gem-difluorocyclopropenylalkynes and 3,3,3′,3′-tetrafluorobicyclopropyl-1,1′-dienes |
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Authors: | Zhan-Ling Cheng |
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Institution: | Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, 200032 Shanghai, China |
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Abstract: | A series of gem-difluorocyclopropenylalkynes are easily obtained in good yields by the Sonogashira reaction of 3,3-difluoro-1-iodocyclopropenes with terminal alkynes. Onto these new alkynes addition of difluorocarbene, generated from the decomposition of FSO2CF2COOTMS in diglme in the presence of 10 mol% anhydrous NaF at 120 °C, gives 3,3,3′,3′-tetrafluorobicyclopropyl-1,1′-dienes. Acid hydrolysis of gem-difluorocyclopropenylalkynes in refluxing CH3OH affords the corresponding methoxycarbonylenynes. |
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Keywords: | 3 3-Difluoro-1-iodocyclopropenes Sonogashira reaction 3 3 3&prime 3&prime -Tetrafluorobicyclopropyl-1 1&prime -dienes Difluorocarbene |
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