The Reaction of α-Carbonyl Sulfides with Bases. I. The Reaction between α-Carbonyl Sulfides with Thiolates

It is found that carbonyl compounds, such as ketones and esters, bearing an alkyl(or aryl)thio group at the α-position, are smoothly reduced to the parent carbonyl compounds by the action of the thiolate anion. α-Halo or α,α-dihalo ketones are similarly reduced with the thiolate, probably via the corresponding sulfides. The mechanism of the reaction is discussed.