A series of S,S-acetals (spiro-1,3-dithiolanes, 1,3-dithiolanes, and S,S-dibenzyl acetals) have been converted into the corresponding carbonyl compounds by sodium nitrite in aqueous solution (NO+, H2ONO+, CINO) or with t-butyl hypochlorite (Cl+) in anhydrous CCl4. Mechanisms for these transformations are suggested, based on the Hard and Soft Acids and Bases (HSAB) principle.
M. T. M. El-Wassimy, K. A. Jørgensen and S.-O. Lawesson, J. Chem. Soc., Perkin Trans. 1, 1983, 2201 DOI: 10.1039/P19830002201
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