Mozingo reduction

The Mozingo reduction, also known as Mozingo reaction or thioketal reduction, is a chemical reaction capable of fully reducing a ketone or aldehyde to the corresponding alkane via a dithioacetal.^[1][2] The reaction scheme is as follows:^[3]

Mozingo reduction
Named after	Ralph Mozingo
Reaction type	Organic redox reaction

The ketone or aldehyde is activated by conversion to cyclic dithioacetal by reaction with a dithiol (nucleophilic substitution) in presence of a H⁺ donating acid. The cyclic dithioacetal structure is then hydrogenolyzed using Raney nickel. Raney nickel is converted irreversibly to nickel sulfide. This method is milder than either the Clemmensen or Wolff-Kishner reductions, which employ strongly acidic or basic conditions, respectively, that might interfere with other functional groups.^[4]

History

The reaction is named after Ralph Mozingo, who reported the cleavage of thioethers with Raney nickel in 1942.^[5] However the modern iteration of the reaction, involving the cyclic dithioacetal, was developed by Melville Wolfrom.^[6]