Metal (Na+, K+, Cs+) Template Effect–Controlled Synthesis of Stereoisomers of Tetrasubstituted (Thia)calix[4]arene Derivatives Containing Sulfonatoalkyl Moieties on the Lower Rim
А. R. Nugmanovaa, L. S. Yakimovaa (https://orcid.org/0000-0003-3956-6637), K. S. Shibaevaa (https://orcid.org/0000-0002-7948-206X), and I. I. Stoikova, * (https://orcid.org/0000-0002-3019-7866)
aA.M. Butlerov Chemistry Institute of Chemistry, Kazan (Volga Region) Federal University, Kazan, 420008 Russia
email: *ivan.stoikov@mail.ru
Received 5 October, 2022
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.
Keywords:
calix[4]arene,
p-tert-butylcalix[4]arene,
p-tert-butylthiacalix[4]arene,
stereoisomer,
template effect,
sultone
DOI: 10.1134/S1070363222120052