PubMed · 11148057
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N Bouloc, N Walshe, M Bradley. Polyethers: a solid-phase iterative approach.. https://doi.org/10.1021/cc0000545
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A new surfactant-mediated separation method was developed for concentrating traces of gold ion in water. The methodology is based on the combination of selective complexation of gold(III) with polyoxyethylene(10)-p-isononylphenyl ether, PONPE-10, and strong binding of surfactant complex to hydrophobic polystyrene resins embedded in a PTFE fiber disk (Empore disk). A 400-fold concentration of gold(III) was achieved by 400 ml load of the sample containing 0.01% (w/v) PONPE-10 and 0.10 M nitric acid and by the subsequent elution with 1.0 ml of aqueous buffer solution of 0.01 M N-(dithiocarboxyl)sarcosine diammonium. Traces of gold (0.40 ng/l) in river water samples were successfully determined with inductively coupled plasma MS.
[reaction: see text] Regioselective 1,3-dipolar cycloadditions of supported vinyl ethers R(1)C(=CH(2))O-CH(2)-polymer, prepared by the Tebbe olefination of R(1)CO(2)-CH(2)-polymer, with ethyl cyanoformate N-oxide gave supported isoxazoline derivatives. Release from the support under mild acidic conditions gave the isoxazoles ethyl 5-R(1)-isoxazole-3-carboxylates. Alternatively, further on-resin functionalization of the R(1) substituent using Suzuki coupling reactions and release from the support under acidic conditions gave more structurally diverse isoxazoles.
[reaction: see text]. Synthesis of novel dithiane-spiro-crown ethers starting from 5,5-di(hydroxymethyl)-1,3-dithiane is developed. These compounds can be used as building blocks to assemble photolabile bis-crown ethers via addition to dicarbonyl-containing tethers, e.g., isophthalic aldehyde. It is found that unlike their mono-crown precursors such bidentate bis-crowns are capable of efficient liquid membrane transport of, for example, methyl viologen. The transport can be interrupted photochemically, providing a basis for developing smart light-responsive membranes.