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Monofluorinated allylic ether 4 was synthesised in 4 steps from trifluoroethanol. Formation of the monofluoro vinyllithium 5 which was stable at up to −50 °C, and subsequent reaction with a wide range of electrophiles gave access to a series of highly functionalised monofluorinated allylic ethers. Effective electrophiles included Group (IV) halides, methyl iodide and benzaldehyde, whilst aliphatic aldehydes proved to be less efficient electrophiles. Use of a monofluoro vinylzinc reagent, prepared by transmetallation of 5 , allowed efficient access to the monofluorovinyl iodide 6e . |
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