Reaction of 4-aryl-1,1,1-trifluorobut-3-en-2-ols [CF3-allyl alcohols, ArCH=CHCH(OH)CF3] with arenes under activation with anhydrous FeCl3 or FSO3H was studied. We found that the transformation led to trifluoromethylated alkenes [Ar(Ar′)CHCH=CHCF3] or 1-trifluoromethylated indanes (CF3-indanes). The formation of these two types of reaction products strongly depends on the nucleophilicity of the starting arene and the electrophilicity of cationic intermediates generated from CF3-allyl alcohols under reaction conditions. Benzene, anisole, veratrole, and ortho-xylene lead exclusively to CF3-alkenes with an E-configuration. More π-donating polymethylated arenes (pseudocumene, mesitylene) afford only CF3-indanes with a predominantly cis-orientation of substituents at positions 1 and 3 of the indane ring. Meta- and para-xylenes show an intermediate behavior; they may form both CF3-alkenes and/or CF3-indanes. The mechanisms of the investigated transformations are discussed.
Original languageEnglish
Pages (from-to)9506-9517
Number of pages12
JournalJournal of Organic Chemistry
Volume80
Issue number19
DOIs
StatePublished - 2015

    Research areas

  • electrophilic reactions, CF3-allylic alcohols, superacids, fluorine eletrophiles, CF3-alkenes, CF3-indanes, electrophilic aromatic substitution

ID: 3973167