TY - JOUR
T1 - Lithiation of meso-octamethylcalix[4]pyrrole
T2 - A general route to C-rim monosubstituted calix[4]pyrroles
AU - Anzenbacher, P
AU - Jursikova, K
AU - Shriver, JA
AU - Miyaji, H
AU - Lynch, VM
AU - Sessler, JL
AU - Gale, PA
PY - 2000
Y1 - 2000
N2 - 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.
AB - 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.
UR - https://publons.com/publon/9474638/
U2 - 10.1021/jo005610w
DO - 10.1021/jo005610w
M3 - Article
SN - 0022-3263
VL - 65
SP - 7641
EP - 7645
JO - The Journal of Organic Chemistry
JF - The Journal of Organic Chemistry
IS - 22
ER -