Metal (Na+, K+, Cs+) Template Effect-Controlled Synthesis of Stereoisomers of Tetrasubstituted (Thia)calix4arene Derivatives Containing Sulfonatoalkyl Moieties on the Lower Rim

摘要

New water-soluble derivatives of thiacalix4arene, p-tert-butylcalix4arene, and p-tert-butylthiacalix4arene 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.