Abstract
1-(1-Methyl-2-pyrrolyl)-2,2,2-trifluoroethyl p-nitrobenzoate (3) reacts by carbocation formation with an m value for the dependence of rate on the solvent polarity parameter YOTs of 0.56, and a rate 41 times slower than (1-methyl-2-pyrrolyl)methyl p-nitrobenzoate. The products from 3 include significant amounts of material derived from solvent attack at the 5-position of the pyrrole ring. The results indicate a high degree of charge delocalization by the strongly donating pyrrolyl group, resulting in a low k(H)/k(CF3) rate ratio and nucleophilic attack on the ring. 1,1, l-Trifluoro-2-(1-methyl-2-pyrrolyl)propan-2-ol (10) reacted with CF3CO2H via a tertiary carbocation, which led to dimeric products resulting from electrophilic substitution on the pyrrole ring. Keywords: pyrrole, trifluoromethyl substituents, carbocations.
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