Document Type
Article
Publication Date
2026
Publication Title
The Journal of Organic Chemistry
Keywords
carbaporphyrinoids, oxidations, aromaticity, macrocycles, pyrrolo[1, 2-B]pyrrole
Abstract
Acid-catalyzed condensation of N-alkyltripyrranes with a cyclopentadiene trialdehyde, followed by oxidation with aqueous ferric chloride solutions, gave unusual tripyrrolic byproducts in addition to previously reported carbaporphyrins and oxycarbaporphyrins. These stable nonaromatic structures incorporate aldehyde substituents, macrocyclic ketones, two conjugated pyrrole units, and a pyrrolo[1,2-a]pyrrole moiety. The NMR and UV-vis data were consistent with a nonaromatic system, and single-crystal X-ray diffraction confirmed that these structures are highly distorted. Structural characterization of a related aromatic carbaporphyrin triketone was also accomplished.
Funding Source
This work was supported by the National Science Foundation under CHE-2247214. NSF is also acknowledged for providing funding for the departmental X-ray diffractometer (CHE-2407904), NMR spectrometers (CHE-0722385), and high-resolution mass spectrometer (CHE-1337497) under the Major Research Instrumentation (MRI) program. This article was published open access thanks to a transformative agreement between Milner Library and ACS.
Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.
DOI
10.1021/acs.joc.6c01802
Recommended Citation
Le, K., Ferrence, G. M., & Lash, T. D. (2026). Spectroscopic and Structural Characterization of Unexpected Porphyrinoid Byproducts Resulting from the Reaction of a Cyclopentadiene Trialdehyde with N-Alkyltripyrranes. The Journal of Organic Chemistry. https://doi.org/10.1021/acs.joc.6c01802
Comments
First published in The Journal of Inorganic Chemistry (2026): https://doi.org/10.1021/acs.joc.6c01802. Supporting information available on the publisher's site.