The title sultone is cleaved in the presence of nucleophiles in aqueous solution via general base-catalysed and nucleophilic pathways. The sensitivity of the nucleophilic reactivity to reagent structure (βN) suggests extensive bond formation in the transition state. Proton transfer for nucleophilic attack by amines occurs after the S–N bond forming process is complete.
T. Deacon, A. Steltner and A. Williams, J. Chem. Soc., Perkin Trans. 2, 1975, 1778 DOI: 10.1039/P29750001778
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