10.1016/j.tetlet.2006.06.131
The study presents an eco-friendly and cost-effective method for converting dithioacetals to carbonyl compounds using oxalic acid as a catalyst. Dithioacetals, which are stable functional groups used as acyl anion equivalents and protecting groups in organic synthesis, are typically challenging to convert into carbonyl compounds due to their stability. Traditional methods often involve toxic heavy metal salts like HgCl2, which pose environmental and disposal challenges. In this research, oxalic acid catalyzes the hydrolysis of dithioacetals in the presence of acetals such as dimethoxymethane (DMM) or diethoxymethane (DEM), yielding carbonyl compounds and bis(dodecylthio)methane. The reaction is effective for both aldehydes and ketones, with nitromethane as the preferred solvent. The study highlights the use of oxalic acid as a green alternative to toxic reagents, offering high yields and recyclability of dithioacetals. The proposed mechanism involves protonation of the acetal, nucleophilic attacks by sulfur atoms, and subsequent eliminations leading to the formation of carbonyl compounds.
