Add time:08/07/2019         Source:sciencedirect.com

Depending on the conditions used during the lithiation and subsequent carboxylation of 1-[(trifluoromethyl)phenyl]pyrroles the mono- and the dicarboxylated derivatives were selectively prepared. The regioselective formation of the monocarboxylic acids could be rationalized in the light of the data collected from the literature. Explanation of the other phenomena, such as regioselective dilithiation and the strong effect of the trifluoromethyl group on the structure and aromaticity of the pyrrole ring in the ortho position, has been elucidated by the aid of molecular modelling and single crystal X-Ray measurements.

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