Abstract
A new protocol for the synthetically useful deprotection of 1,3-dithiolane and 1,3-oxathiolane protected moieties has been developed. A series of 2,2-disubstituted 1,3 – dithiolanes and 1,3 – oxathiolanes was effectively deprotected to release the corresponding carbonyl compounds. The combination of trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl-ethaneperoxate and KOH was shown to be an effective system for the oxidative cleavage of C–S bonds under mild reaction conditions at room temperature. The active oxidizing specie is singlet molecular oxygen. It is generated via fragmentation of the trans-5-hydroperoxy-3,5-dimethyl-1,2 – dioxolane-3-yl ethaneperoxate with the help of KOH.
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