1,10-diaza-18-crown-ether, modified by phosphonate pendant arms - Synthesis, structure, and picrate extraction properties

Abstract

Reaction of O,O′-diisopropyl-3-methyl-1,2-butadienylphosphonate with 1,10-diaza-18-crown-6 in the presence of a catalytic amount of iPrONa leads to the new crown-ether derivative, containing phosphonate pendant arms (L). The structure of the compound obtained was investigated by single crystal X-ray diffraction analysis, IR, 1H and 31P{1H} NMR spectroscopy, and microanalysis. In the crystal structure the side arms of L are in an anti disposition relative to the macrocyclic cavity. It was established that phosphorylation of 1,10-diaza-18-crown-6 by allenylphosphonate results in an increase of extraction of NaPic and KPic, whereas LiPic and NH4Pic are extracted practically in the same level. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.