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Synthesis and cycloaddition of N-substituted pyrroles with polyfluorinated substituents

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Abstract

Reactions of N-pyrrolylpotassium with fluorinated electrophiles yielded N-substituted pyrroles containing polyfluoroalkyl, polyfluoroalkenyl, polyfluoroalkylsulfonyl, and polyfluoroaryl substituents. N-Polyfluoro-substituted pyrroles did not isomerize at ≥100 °C; they were found to be reactive in [4+2] cycloaddition reactions with perfluorobut-2-yne.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1890–1895, August, 2005.

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Moiseev, S.V., Vasil'ev, N.V. Synthesis and cycloaddition of N-substituted pyrroles with polyfluorinated substituents. Russ Chem Bull 54, 1948–1953 (2005). https://doi.org/10.1007/s11172-006-0063-z

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  • DOI: https://doi.org/10.1007/s11172-006-0063-z

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