Polymer-Supported Cryptands. Problems Arising in the Synthesis of Highly Loaded Polymers

Article abstract of DOI:10.1021/jo00375a028

The attachment of a hydroxymethyl<2.2.2>cryptand to lightly loaded chloromethylpolystyrene (<*>1 mequiv of Cl/g) cross-linked with divinylbenzene leads to polymer-supported cryptands that are highly efficient catalysts in anion-promoted reactions carried out under phase-transfer conditions.However, the condensation with polystyrenes having a higher content of chloromethyl groups occurs in low yields, apparently affording immobilized cryptands with very low catalytic activity.This behavior results from extensive structural modifications of the bicyclic ligand, most likely promoted by neighboring chloromethyl groups.