Efficient hydrolysis of dithioacetals by the N-fluoro-2,4,6-trimethylpyridinium triflate-water system

Abstract

Dithioacetals including 1,3-dithianes and 1,3-dithiolanes are efficiently cleaved by the title reagent system to the parent carbonyl compounds. The cleavage of diprotected symmetrical α-diketones and p-phenylenediketones gives monoketones in good yields. Amide, 1,3-dioxolane, disulfide, ester, ether, hydroxy, nitrile, nitro, and sulfide functions are relatively stable under the cleavage conditions but thiols are oxidized to disulfides.