Formation and reactivity of 1-pyrrolyl-2, 2, 2-trifluoroethyl cations

…, JM Kwong-Chip, WC Lin, P Nguyen…

Index: Allen, Annette D.; Kwong-Chip, Jean-Marc; Lin, Wing Cheung; Nguyen, Paul; Tidwell, Thomas T. Canadian Journal of Chemistry, 1990 , vol. 68, # 10 p. 1709 - 1713

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Citation Number: 11

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 Y OTs 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 ...