Journal
JOURNAL OF PORPHYRINS AND PHTHALOCYANINES
Volume 13, Issue 3, Pages 322-325Publisher
WORLD SCI PUBL CO INC
DOI: 10.1142/S1088424609000401
Keywords
calix[4] pyrrole; macrocycle; pyrrole
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Funding
- National Science Foundation [CHE-0749571]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0749571] Funding Source: National Science Foundation
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Calix[4]pyrroles have attracted considerable attention within the macrocyclic, supramolecular, and porphyrin analog communities due to their ability to act as simple-to-synthesize receptors for common anions, such as chloride and fluoride. Reported here is what we believe is a new, potentially generalizable route to fully beta-alkyl substituted calixpyrroles. These products are accessible from the starting pyrrolic esters, and are obtained via simple reaction with CH3Li, followed by subsequent quenching with HCl in ether. A representative system has been characterized by X-ray diffraction analysis. The present route allows access to calix[4] pyrroles bearing functionality, such as double bonds, off the so-called C-rim; such systems are of interest because they could allow for further synthetic elaborations and permit incorporation of calix[4] pyrroles into more complex structures.
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