Abstract
A simple synthesis of 2,8-dithiacalix[4]arene 6 comprising two types of bridges (–CH2– and –S–) within a basic macrocyclic skeleton is reported. By optimizing the method we were able to replace 4 steps of the original stepwise procedure with one step in >50% yield, allowing multigram synthesis of the macrocycle. As documented by the 1H NMR study, the presence of a mixed-bridge system enables direct observation of the so-called flip-flop rearrangement of the hydrogen bond array on the lower rim of the macrocycle. Moreover, the preliminary results showed quite unusual conformational outcomes for the alkylation reactions. The structure of the alkylated macrocycle was confirmed by single crystal X-ray analysis.
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