Fluoroalcohol

Fluoroalcohols are organofluorine compounds consisting of an alcohol functional group with at least one C-F bond. These compounds often have distinctive solvent properties.[1]

Perfluoroalcohols

Most primary and secondary perfluoroalcohols are unstable, for example trifluoromethanol eliminates hydrogen fluoride, forming carbonyl fluoride.[2] This reaction is reversible.[3]

CF₃OH → COF₂ + HF

Stable perfluorinated alcohols include nonafluoro-tert-butyl alcohol ((CF₃)₃COH) and pentafluorophenol (C₆F₅OH).

Partially fluorinated alcohols

Numerous partially fluorinated alcohols are known and have useable stabilities. Trifluoroethanol and hexafluoroisopropanol are used as solvents in research.[4] Fluorotelomer alcohols are precursors to perfluorocarboxylic acids. Pirkle's alcohol is used a chiral shift reagent in nuclear magnetic resonance spectroscopy.

References

Ivan A. Shuklov; Natalia V. Dubrovina; Armin Börner (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis: Benefits from the Use of Fluorinated Alcohols in Homogeneous Catalysis". Synthesis: 2925–2943. doi:10.1055/s-2007-983902.
Schneider, W. F. (1996). "Energetics and Mechanism of Decomposition of CF₃OH". J. Phys. Chem. 100 (15): 6097–6103. doi:10.1021/jp952703m.
Cheburkov, Yuri; Lillquist, Gerald J. (2002). "Perfluoroalcohols". Journal of Fluorine Chemistry. 118 (1–2): 123–126. doi:10.1016/S0022-1139(02)00204-X.
Colomer, Ignacio; Chamberlain, Anna E. R.; Haughey, Maxwell B.; Donohoe, Timothy J. (2017). "Hexafluoroisopropanol as a Highly Versatile Solvent". Nature Reviews Chemistry. 1 (11). doi:10.1038/s41570-017-0088.

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[1] Ivan A. Shuklov; Natalia V. Dubrovina; Armin Börner (2007). "Fluorinated Alcohols as Solvents, Cosolvents and Additives in Homogeneous Catalysis: Benefits from the Use of Fluorinated Alcohols in Homogeneous Catalysis". Synthesis: 2925–2943. doi:10.1055/s-2007-983902.

[2] Schneider, W. F. (1996). "Energetics and Mechanism of Decomposition of CF₃OH". J. Phys. Chem. 100 (15): 6097–6103. doi:10.1021/jp952703m.

[3] Cheburkov, Yuri; Lillquist, Gerald J. (2002). "Perfluoroalcohols". Journal of Fluorine Chemistry. 118 (1–2): 123–126. doi:10.1016/S0022-1139(02)00204-X.

[Nature-4] Colomer, Ignacio; Chamberlain, Anna E. R.; Haughey, Maxwell B.; Donohoe, Timothy J. (2017). "Hexafluoroisopropanol as a Highly Versatile Solvent". Nature Reviews Chemistry. 1 (11). doi:10.1038/s41570-017-0088.