Lithiation of meso-octamethylcalix[4]pyrrole: a general route to C-rim monosubstituted calix[4]pyrroles

Anzenbacher Jr, Pavel, Jursíková, Karolina, Shriver, James A., Miyaji, Hidekazu, Lynch, Vincent M., Sessler, Jonathan L. and Gale, Philip A. (2000) Lithiation of meso-octamethylcalix[4]pyrrole: a general route to C-rim monosubstituted calix[4]pyrroles. Journal of Organic Chemistry, 65, 7641-7645. (doi:10.1021/jo005610w).

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.

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