Synthesis of calix[4]arene derivatives with alkyl guanidinium or chiral bicyclic guanidinium

Citation
F. Liu et al., Synthesis of calix[4]arene derivatives with alkyl guanidinium or chiral bicyclic guanidinium, SYNTHESIS-S, (4), 2001, pp. 607-611
Citations number
24
Language
INGLESE
art.tipo
Article
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
SYNTHESIS-STUTTGART
ISSN journal
0039-7881 → ACNP
Issue
4
Year of publication
2001
Pages
607 - 611
Database
ISI
SICI code
0039-7881(200104):4<607:SOCDWA>2.0.ZU;2-U
Abstract
A series of p-tetra-tert-butyl calix[4]arene derivatives with alkyl guanidi nium or chiral bicyclic guanidinium functionalities were synthesized as the receptors of organic anions. Mono- and di- alkyl guanidinium derivatives w ere prepared by the reaction of 5,11,17,23-tetra-tert-butyl-25,27-(2-aminoe thoxy)-26,28-dihydroxy calix[4]arene (1) with methyl isothiourea sulphate. While mono- and di- chiral bicyclic guanicinium derivatives were all obtain ed via an O-alkylation reaction of p-tetra-tert-butyl calix[4]arene with ch loromethyl chiral bicyclic guanidinium (6 or 7) in the presence of anhydrou s K2CO3 in acetonitrile, good yields were only observed for mono- substitut ed derivatives.