Novel resorcinarene cavitand-based CMP(O) cation ligands: synthesis and extraction properties

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Boerrigter, Harold and Verboom, Willem and Reinhoudt, David N. (1997) Novel resorcinarene cavitand-based CMP(O) cation ligands: synthesis and extraction properties. Journal of Organic Chemistry, 62 (21). pp. 7148-7155. ISSN 0022-3263

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Abstract:Tetrafunctionalized resorcinarene cavitands (4−6) have been synthesized starting from tetrakis(bromomethyl)cavitand 3. New cavitand-based cation ligands with (carbamoylmethyl)phosphonate (CMP) and -phosphine oxide (CMPO) moieties (8a,b and 9a,b) were prepared via two different routes in good (45−86%) overall yields. The ligands (8a,b and 9b) are very effective europium extractants. Ph2CMPON(Pr)-cavitand 8b has the highest extraction constant, determined with radiotracer experiments, for 1:1 complexation with Eu(picrate)3 (Kex1 = 2.7 × 1012 M-4). The steric preorganization of the four CMP(O) moieties on the resorcinarene cavitand improves the efficiency and selectivity [of Eu(III) over UO2(II) and Fe(III)] of the metal extraction processes, compared to simple CMP(O) extractants.
Item Type:Article
Copyright:© 1997 American Chemical Society
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Science and Technology (TNW)
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Link to this item:http://purl.utwente.nl/publications/10976
Official URL:http://dx.doi.org/10.1021/jo9703414
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Metis ID: 105932