Mozingo reduction

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Mozingo reduction
Named after Ralph Mozingo
Reaction type Organic redox reaction

The Mozingo reduction, also known as Mozingo reaction or thioketal reduction, is a

dithioacetal.[1][2] The reaction scheme is as follows:[3]

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]

References