Regioselective Upper Rim Substitution of Calix[4]arenes

0420983 - ÚCHP 2014 RIV GB eng J - Journal Article
Hudeček, O. - Cuřínová, Petra - Budka, J. - Lhoták, P.
Regioselective Upper Rim Substitution of Calix[4]arenes.
Tetrahedron. Roč. 67, č. 29 (2011), s. 5213-5218. ISSN 0040-4020. E-ISSN 1464-5416
R&D Projects: GA ČR GA203/09/0691; GA AV ČR IAAX08240901
Institutional support: RVO:67985858
Keywords : calixarene * electrophilic substitution * anion recognition
Subject RIV: CC - Organic Chemistry
Impact factor: 3.025, year: 2011

The electrophilic substitution of 25,27-dipropoxy-26,28-dinosyloxycalix[4]arene leads exclusively to the para-substitution of the alkylated phenol rings, while in the next step, the protecting nosyl group can be easily removed using a basic hydrolysis. The overall process yields dialkoxycalix[4]arenes with the substitution on the alkylated rings—the substitution pattern, which is complementary to the common dialkoxycalix[4]arenes with substituted nonalkylated phenolic units. The usefulness of this protection/deprotection procedure was documented by the synthesis of novel type of calixarene dipropoxy derivatives, and by the preparation of a novel anion receptor based on this substitution pattern.
Permanent Link: http://hdl.handle.net/11104/0227460