6533b7dafe1ef96bd126ead1

RESEARCH PRODUCT

Regioselective synthesis of calixcrowns derived from p-tert-butylcalix[5]arene

Ralf ArneckeWalter VogtDagmar KraftVolker Böhmer

subject

chemistry.chemical_classificationStereochemistryOrganic ChemistryRegioselectivityAlkylationBiochemistryMedicinal chemistrychemistry.chemical_compoundPolycyclic compoundchemistryYield (chemistry)Drug DiscoveryCalixareneHexaethylene glycolCyclophane

description

Abstract Alkylation of p-tert-butylcalix[5]arene with oligoethylene glycol-ditosylates in the presence of CsF affords the 1,3-bridged calix[5]crowns 1a–c in 51 to 72% yield. In the case of hexaethylene glycol the isomeric 1,2-bridged calix[5]crown-7 2c was obtained additionally. The calixcrowns were further modified by alkylation of the remaining hydroxyl groups.

https://doi.org/10.1016/s0040-4020(01)87186-6