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Metal (Na+, K+, Cs+) Template Effect–Controlled Synthesis of Stereoisomers of Tetrasubstituted (Thia)calix[4]arene Derivatives Containing Sulfonatoalkyl Moieties on the Lower Rim

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Abstract

New water-soluble derivatives of thiacalix[4]arene, p-tert-butylcalix[4]arene, and p-tert-butylthiacalix[4]arene with sulfonatopropyl- and sulfonatobutyl moieties on the lower rim were synthesized. The template effect of alkali metal cations (Na+, K+, Cs+) on the configuration of products formed in the alkylation reaction of lower rim with 1,3-propane- and 1,4-butanesultone was revealed. In the case of Na+, the cone stereoisomer was formed exclusively, while with K+ and Cs+, mixtures of stereoisomers (cone, partial cone, and 1,3-alternate) were obtained.

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Funding

The work was financially supported by the Russian Science Foundation (project no. 18-73-10094, https://rscf.ru/project/18-73-10094/).

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Authors and Affiliations

  1. A.M. Butlerov Chemistry Institute of Chemistry, Kazan (Volga Region) Federal University, 420008, Kazan, Russia

    А. R. Nugmanova, L. S. Yakimova, K. S. Shibaeva & I. I. Stoikov

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  1. А. R. Nugmanova
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  2. L. S. Yakimova
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  3. K. S. Shibaeva
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  4. I. I. Stoikov
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Correspondence to I. I. Stoikov.

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To the 145th anniversary of A.E. Arbuzov

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Nugmanova, А.R., Yakimova, L.S., Shibaeva, K.S. et al. Metal (Na+, K+, Cs+) Template Effect–Controlled Synthesis of Stereoisomers of Tetrasubstituted (Thia)calix[4]arene Derivatives Containing Sulfonatoalkyl Moieties on the Lower Rim. Russ J Gen Chem 92, 2582–2589 (2022). https://doi.org/10.1134/S1070363222120052

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