Octacarbamoylated and octathiocarbamoylated resorcinarenes: transformations and acceptor properties

Abstract

A series of octa(thio)carbamoylated resorcinarenes was synthesized by the reactions of rccc-resorcinarenes with N,N-dimethylcarbamoyl and N,N-dimethylthiocarbamoyl chlorides in the presence of alkali carbonates. The derivatives with thiocarbamoyl groups were transformed into octa(carbamoylthio)resorcinarenes by the thione—thiol rearrangement. In a homogeneous medium octacarbamoylated resorcinarenes demonstrated high acceptor properties and selectivity to cesium cations but manifested low extraction ability towards alkali metal cations from the aqueous phase to organic one because of the formation of stable films at the interface. Resorcinarenes with thiocarbamoyl and carbamoylthio groups are capable of extracting lanthanides (Nd³⁺, Yb³⁺) from aqueous media and are selective to Nd³⁺ cations.