Synthesis and Alkali Metal Picrate Extraction Capabilities of Novel Bis(benzocrown Ethers) Based on Diphenylglycoluril

Alexander Yu. Lyapunov, Victor N. Pastushok, Tatyana I. Kirichenko, Catherine Yu. Kulygina, Leonid S. Kikot’, Tatyana Yu. Bogaschenko, and Nikolay G. Luk’yanenko^@

A.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa, 65080, Ukraine

^@Corresponding author E-mail: ngl@farlep.net

DOI: 10.6060/mhc2010.1.86

Macroheterocycles 2010 3(1) 86-92

Novel glycoluril-bridged bis(benzocrown ethers) have been synthesized. The appropriate bis(benzo-18-crown-6) was formed in a good yield by reaction of bis(cyclomethoxymethylene)diphenylglycoluril with benzo-18-crown-6 in polyphosphoric acid. The reaction with dibenzo-18-crown-6 under the same conditions leads only to polymeric products. The corresponding bis(dibenzo-18-crown-6) was prepared in moderate yield by the reaction of tetrakis(chloromethyl)diphenylglycoluril with the dibenzo-18-crown-6 in the presence of SnCl4 in dichloroethane. Extraction of alkali metal picrates from water into chloroform by bis(benzocrown ethers) was examined to estimate their complexation ability. The extraction capability of bis(benzocrown ethers) is much greater than of the corresponding monomeric crown ethers.

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