The Elusive beta-unsubstituted calix[5]pyrrole finally captured

Grazia Cafeo; Franz H Kohnke; Melchiorre F Parisi; Rosetta Pistone Nascone; Giovanna L La Torre; David J Williams

doi:10.1021/ol0262082

The Elusive beta-unsubstituted calix[5]pyrrole finally captured

Org Lett. 2002 Aug 8;4(16):2695-7. doi: 10.1021/ol0262082.

Authors

Grazia Cafeo¹, Franz H Kohnke, Melchiorre F Parisi, Rosetta Pistone Nascone, Giovanna L La Torre, David J Williams

Affiliation

¹ Dipartimento di Chimica Organica e Biologica, Università di Messina, Salita Sperone 31, I-98166 Messina, Italy.

PMID: 12153212
DOI: 10.1021/ol0262082

Abstract

[reaction: see text] The meso-decamethyl-calix[5]pyrrole 2b was synthesized from the furan-based analogue 1b via the homologation of the furan rings to pyrrole, and its solid-state structure was determined by X-ray crystallography: surprisingly, the binding constant of 2b toward chloride is found to be lower than that of the tetrameric analogue 2a.