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A model system is introduced as a general tool to elaborate on orthogonal templation of dynamic covalent ring‐opening polymerization (ODC‐TROP). The tool consists of 310 helical peptides as unprecedented templates and semicarbazones as orthogonal dynamic covalent linkers. With difficult‐to‐control 1,2‐dithiolanes, ODC‐TROP on the level of short model oligomers occurs with high templation efficiency,...
The thiol‐mediated opening of 3‐alkyl‐1,2‐dithiolanes and diselenolanes is described. The thiolate nucleophile is shown to react specifically with the secondary chalcogen atom, against steric demand, probably because the primary chalcogen atom provides a better leaving group. Once released, this primary chalcogen atom reacts with the obtained secondary dichalcogenide to produce the constitutional...
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