| Abstrakt: |
This study explores a thiol‐free, two‐step synthetic strategy to intricate thiacyclophanes from bromoaryl precursors. Our methodology involves a one‐pot substitution reaction of aryl bromides with potassium thioacetate (PTA) followed by ring‐closing metathesis (RCM). Potassium thioacetate is advantageous over other sulfur‐containing reagents like sodium sulfide, sodium hydrosulfide, and sodium hydroxymethylsulfinate (rongalite), etc., as it generates a stable and odorless thioacetate intermediate which allows access to a variety of symmetrical and unsymmetrical sulfides. These sulfides undergo RCM to generate new thiacyclophanes. Applying this methodology, we have created 24 new oxa‐thiacyclophanes and aza‐oxa‐thiacyclophanes containing different aromatic and aliphatic units. The structures and stereochemistry of these cyclophanes are confirmed by NMR data and further supported by single‐crystal X‐ray diffraction data. • A thiol free, two‐step synthetic strategy to new thiacyclophanes using ring‐closing metathesis (RCM) reaction as key step. • Potassium thioacetate as sulfur source, which is odorless and stable as compared to other reagents like sodium sulphide and sodium hydrosulphide. • Synthesis of all starting materials involve simple and inexpensive procedures. • 23 new oxa‐thiacyclophanes and aza‐oxathiacyclophanes were synthesized and characterized by NMR data and single‐crystal x‐ray diffraction data. |
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