Abstract
Triflic acid catalyzed Friedel-Crafts alkylation of aromatics with mono- and bis(trifluoromethyl)oxiranes through ring opening afforded α-(trifluoromethyl) and α,α-bis(trifluoromethyl)-β-phenylethanols in excellent yields. The regioselectivity of the oxirane ring opening and subsequent Friedel-Crafts alkylation have been found to depend on the electronic and steric effects of the substituents in the oxirane ring. DFT studies show that C2-O bond is longer than C1-O bond due to high electron-withdrawing effect of CF3 groups effecting C2-O cleavage resulting in a C2 electrophilic center promoting electrophilic substitution with the C2 center on aromatics.
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