Collection of Czechoslovak Chemical Communications - digital archive 

Abstract

Reactions of 4-phenylbut-3-yn-2-one (1a) and phenylpropynal (1b) with trimethyl(perfluoroalkyl)silanes (Me₃SiR_f) (R_f = CF₃, C₂F₅, n-C₆F₁₃, n-C₇F₁₅, n-C₈F₁₇) in the presence of catalytic amounts of cesium fluoride (CsF) have been studied. Compounds 1a, 1b were reacted with 0.5 equivalent excess of Me₃SiR_f in ethylene glycol dimethyl ether (monoglyme) at 25 °C for R_f = CF₃, C₂F₅ and at 50 °C for R_f = n-C₆F₁₃, n-C₇F₁₅, n-C₈F₁₇ to give the corresponding perfluoroalkylated alcohols in good yields after acid hydrolysis. The new compounds were characterized by IR, NMR (¹H, ¹⁹F, ¹³C), MS and elemental analysis. In these reactions, tetrabutylammonium fluoride (TBAF) is also effective as the fluoride catalyst. The alcohols with CF₃ or C₂F₅ are viscous liquids whereas those with n-C₆F₁₃, n-C₇F₁₅ or n-C₈F₁₇ are solids. They are soluble in common organic solvents and stable to air and moisture.

Keywords: Fluoride; Nucleophilic additions; Perfluoroakylations; Ketones; Aldehydes; Alkynes; Trimethyl(perfluoroalkyl)silanes.

References: 41 live references.