Lithiation of meso-octamethylcalix[4]pyrrole: a general route to C-Rim monosubstituted calix[4]pyrroles |
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Authors: | Anzenbacher P Jursíková K Shriver J A Miyaji H Lynch V M Sessler J L Gale P A |
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Institution: | Department of Chemistry and Biochemistry and Institute for Cellular and Molecular Biology, University of Texas at Austin, Austin, Texas 78712-1167, USA. |
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Abstract: | Lithiation and subsequent addition of an electrophile to meso-octamethylcalix4]pyrrole provides a straightforward synthetic route to new, C-rim monosubstituted calix4]pyrroles. A variety of electrophiles were used, resulting in calix4]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 calix4]pyrrole derivatives themselves. |
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