The trifluoromethyl-λ6-tetrafluorosulfanyl (CF3SF4) group remains relatively unexplored in comparison with that of the SF5 and CF3 groups. This paucity of information is largely due to the difficulty of preparing and handling the CF3SF4 group. Research exploring the CF3SF4 group has shown that the properties of this group are consistent with those associated with polar hydrophobicity, reduced desolvation energy along with retention of a significant dipole moment. The CF3SF4 group can be introduced by the addition of trifluoromethyl-λ6-tetrafluorosulfanyl chloride (CF3SF4Cl )to alkenes or alkynes. Initial fluoride ion displacement of the chloride leaving groups can be followed by oxidative chlorofluorination to form CF3SF4Cl from readily available perchloromethyl chloride. The reactivity of CF3SF4-substituted molecules has been explored, creating a variety CF3SF4- substituted building blocks. In this work focus will be on simple two-carbon building blocks, such as CF3SF4-acetic acid, 2-CF3SF4-ethanol and 2-CF3SF4-ethyl halides.

Trifluoromethyl-λ6-tetrafluorosulfanyl-substituted two-carbon building blocks: New tools for the introduction of polar hydrophobicity

255th National Meeting (2018)

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