Lithiation of meso-octamethylcalix[4]pyrrole: a general route to C-Rim monosubstituted calix[4]pyrroles.
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.
Anzenbacher
P
P
Department of Chemistry and Biochemistry and Institute for Cellular and Molecular Biology, University of Texas at Austin, Austin, Texas 78712-1167, USA.
Jursíková
K
K
Shriver
J A
JA
Miyaji
H
H
Lynch
V M
VM
Sessler
J L
JL
Gale
P A
PA
D007202:Indicators and Reagents; D008094:Lithium / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D011758:Pyrroles; D008094:Lithium