title: Lithiation of meso-octamethylcalix[4]pyrrole: a general route to C-Rim monosubstituted calix[4]pyrroles.
abstract: Lithiation and subsequent addition of an electrophile to meso-octamethylcalix[4]pyrrole provides a straightforward synthetic route to new, C-rim monosubstituted calix[4]pyrroles. A variety of electrophiles were used, resulting in calix[4]pyrroles with appended functional groups including carboxyl, ester, iodo, and formyl. This method was optimized to give maximum yields of the monosubstituted derivatives with lowest possible contamination by di- and trisubstituted congeners. Solid-state studies, performed for a number of these derivatives, showed unexpected supramolecular interactions involving both solvents and the monosubstituted calix[4]pyrrole derivatives themselves.
authors.affiliation: Department of Chemistry and Biochemistry and Institute for Cellular and Molecular Biology, University of Texas at Austin, Austin, Texas 78712-1167, USA.
authors.forename: P
authors.initials: P
authors.lastname: Anzenbacher
authors.forename: K
authors.initials: K
authors.lastname: Jursíková
authors.forename: J A
authors.initials: JA
authors.lastname: Shriver
authors.forename: H
authors.initials: H
authors.lastname: Miyaji
authors.forename: V M
authors.initials: VM
authors.lastname: Lynch
authors.forename: J L
authors.initials: JL
authors.lastname: Sessler
authors.forename: P A
authors.initials: PA
authors.lastname: Gale
mesh_terms: D007202:Indicators and Reagents; D008094:Lithium / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis*
chemical_list: D007202:Indicators and Reagents; D011758:Pyrroles; D008094:Lithium