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N-Confused Calix
Depraetere1, Smet, Dehaen
1Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, BE-3001 Heverlee (Belgium).
Angewandte Chemie (International Ed. in English)
|December 22, 1999
Summary
N-confused calix[4]pyrroles are formed as significant side products during the acid-catalyzed reaction of ketones and pyrrole. This discovery highlights a new pathway in macrocycle synthesis.
Area of Science:
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Calix[4]pyrroles are macrocyclic compounds with diverse applications.
- Their synthesis typically involves the acid-catalyzed condensation of pyrrole and ketones.
Purpose of the Study:
- To investigate the side products formed during the synthesis of calix[4]pyrroles.
- To characterize the N-confused calix[4]pyrrole isomers.
Main Methods:
- Acid-catalyzed condensation reaction of ketones and pyrrole.
- Isolation and characterization of reaction products using spectroscopic techniques.
Main Results:
- The formation of N-confused calix[4]pyrrole (2) as a significant side product, with yields up to 22%.
- Identification of doubly N-confused calix[4]pyrroles in some reaction mixtures.
- The study details the unexpected co-formation of these isomers alongside the target calix[4]pyrrole (1).
Conclusions:
- The acid-catalyzed condensation of pyrrole and ketones can lead to the formation of N-confused calix[4]pyrroles.
- This finding expands the known synthetic pathways for calixpyrrole derivatives.
- Further research may explore controlling the formation of these N-confused isomers.