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]

CF
3OH ⇌ COF
2 + HF (I)

Stable perfluorinated alcohols include nonafluoro-tert-butyl alcohol ((CF3)3COH), hexafluoroisopropanol ((CF3)2CHOH) and pentafluorophenol (C6F5OH).

Partially fluorinated alcohols

Numerous partially fluorinated alcohols are known. Trifluoroethanol is a popular solvent. Fluorotelomer alcohols are precursors to perfluorocarboxylic acids. Pirkle's alcohol is used a chiral shift reagent in nuclear magnetic resonance spectroscopy.

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References
  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.CS1 maint: uses authors parameter (link)
  2. Schneider, W. F. (1996). "Energetics and Mechanism of Decomposition of CF3OH". J. Phys. Chem. 100: 6097–6103. doi:10.1021/jp952703m.
  3. Cheburkov, Yuri; Lillquist, Gerald J. (2002). "Perfluoroalcohols". Journal of Fluorine Chemistry. 118: 123–126. doi:10.1016/S0022-1139(02)00204-X.CS1 maint: uses authors parameter (link)
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