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


A thioketal is first produced by reaction of the ketone with an appropriate thiol. The product is then hydrogenolyzed to the alkane, using Raney nickel. It is sometimes incorrectly stated that Raney nickel is a catalyst in this process. In fact, stoichiometric amounts of Raney nickel must be employed because the sulfur atoms are ultimately converted to catalytically inactive nickel sulfides. Nevertheless, this method is much milder than either the Clemmensen or Wolff-Kishner reductions, which employ strongly acidic or basic conditions, respectively, that might interfere with other functional groups present in the molecule.[4]

See also

References

  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.
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