The S,S-acetal to carbonyl transformation using the soft NO+or Cl+species

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Abstract
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.