33741-68-3Relevant academic research and scientific papers
(E)-Trimethyl(perfluoroprop-1-enyl)silane as a reagent to transfer perfluoroprop-1-enyl group to ketones and aldehydes catalyzed by fluoride
Larichev, Roman B.,Petrov, Viacheslav A.,Grier, Gerard J.,Nappa, Mario J.,Marshall, William J.,Marchione, Alexander A.,Dooley, Rebecca J.
, p. 1060 - 1066 (2014)
Analogous to trifluoromethyltrimethylsilane (Ruppert's reagent) (E)-trimethyl(perfluoroprop-1-enyl)silane (1), prepared by deprotonation of (Z)-1,2,3,3,3-pentafluoroprop-1-ene (2a) at -78 °C in the presence of chlorotrimethylsilane, was shown to transfer the perfluoroprop-1-enyl group to a number of electrophiles containing carbonyl group in the presence of catalytic amount of fluoride anion. The perfluoroprop-1-enyl group was transferred to formaldehyde, acetaldehyde, benzaldehyde, acetone, trifluoroacetophenone resulting in formation of corresponding TMS-ethers of secondary and tertiary alcohols containing Z-CF3CF=CF- fragment. With some substrates such as hexafluoroacetone, formaldehyde, and trifluoroacetophenone, substituted 5-membered dioxolane products of the reaction can be obtained, depending on the reaction conditions and the source of fluoride catalyst.
