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-CF3CFCF–
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.