- Synthesis of a Chiral 3,3′-Di-tert-butyl-2,2′-bipyrrole
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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°.
- Skowronek, Pawel,Lightner, David A.
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- tert-butyl-substituted tripyrranes: Insights into the steric and conformational factors that influence porphyrinoid ring formation in the "3 + 1" methodology
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The MacDonald "3 + 1" route for porphyrinoid synthesis involves the acid-catalyzed condensation of tripyrranes with monocyclic dialdehydes, followed by an oxidation step. In the present study, yields were found to be greatly diminished when tert-butyl sub
- Jiao, Wenhua,Lash, Timothy D.
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p. 3896 - 3901
(2007/10/03)
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