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.
Similar content being viewed by others
References
Ch. S. Cleaver and D. C. England, Du Pont de Nemours and Co., US Pat. 2,861,990, Nov. 25, 1958; Chem. Abstr., 1959, 53, 14123.
D. C. England, L. R. Melbi, M. A. Dietrich, and R. V. Lindsey, Jr., J. Am. Chem. Soc., 1960, 82, 5116.
U. Jager and W. Sundermeyer, Chem. Ber., 1986, 119, 3405.
H. Fischer and H. Orth, Die Chemie des Pyrrols, J. Springer, Berlin, 1934, Bd. I.
S. Benefice-Malqueit, H. Blancou, R. Teissedre, and A. Commeyras, J. Fluorine Chem., 1986, 31, 319.
J. C. Blazejewski, D. Cantacuzene, and C. Wakselman, Tetrahedron Lett., 1975, 6, 363.
R. Kitzing, R. Fuchs, M. Joeux, and H. Prinzbach, Helv. Chim. Acta, 1968, 51, 888.
A. Gordon and R. Ford, Chemist's Companion. A Handbook of Practical Data, Techniques, and References, Wiley Interscience, New York—London—Toronto, 1972.
Author information
Authors and Affiliations
Additional information
__________
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1890–1895, August, 2005.
Rights and permissions
About this article
Cite this article
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
Received:
Revised:
Issue Date:
DOI: https://doi.org/10.1007/s11172-006-0063-z