Summary.
Diethyl 3,3′-di-tert-butyl-4,4′-dimethyl-2,2′-bipyrrole-5,5′-dicarboxylate was synthesized in four steps from ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate. The CH2 hydrogens of the ethyl ester groups of the former are diastereotopic in the 1H-NMR, consistent with axial chirality of the bipyrrole and restricted rotation about the 2,2′-bipyrrole bond, due to the tert-butyl groups. An X-ray structure of the crystalline target compound shows the pyrrole rings are twisted out of coplanarity by 84.5°.
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Corresponding author. E-mail: lightner@scs.unr.edu
Received September 2, 2002; accepted September 13, 2002 Published online February 20, 2003
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Skowronek, P., Lightner, D. Synthesis of a Chiral 3,3′-Di-tert-butyl-2,2′-bipyrrole. Monatshefte füer Chemie 134, 889–899 (2003). https://doi.org/10.1007/s00706-002-0562-z
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DOI: https://doi.org/10.1007/s00706-002-0562-z