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 chemical reaction capable of fully reducing a ketone or aldehyde to the corresponding alkane.[1] [2] The reaction scheme is as follows:[3]

Mozingo reaction.svg


The ketone or aldehyde is activated by conversion to dithioketal or dithioacetal by reaction with a dithiol. The dithio 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]

References[edit]

  1. ^ Francis A. Carey; Richard J. Sundberg (2007). Advanced Organic Chemistry: Reactions and synthesis. Springer. pp. 452–454. ISBN 9780387683508. 
  2. ^ Mosettig, E. and Mozingo, R. 2011. The Rosenmund Reduction of Acid Chlorides to Aldehydes. Organic Reactions. 4:7:362–377. doi:10.1002/0471264180.or004.07
  3. ^ Jonathan Clayden; Nick Greeves; Stuart Warren (2012). Organic Chemistry (2 ed.). Oxford University Press. ISBN 9780199270293. 
  4. ^ Mithcell, Reginald; Lai, Yee-Hing (1980). "The neutral deoxygenation (reduction) of aryl carbonyl compounds with raney-nickel. an alternative to the clemmenson, wolf-kishner or mozingo (thioketal) reductions". Tetrahedron Letters. Elsevier. 21 (27): 2637–2638. doi:10.1016/S0040-4039(00)92825-9. Retrieved 2012-05-11.