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

chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass changes that only involve the positions of electrons in the forming and break ...

capable of fully reducing a

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bon ...

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group ...

to the corresponding

alkane In organic chemistry Organic chemistry is a subdiscipline within chemistry involving the science, scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms tha ...

via a

dithioacetal In organosulfur chemistry, thioacetals are the sulfur ('' thio-'') analogues of acetals (). There are two classes: the less-common monothioacetals, with the formula , and the dithioacetals, with the formula (symmetric dithioacetals) or (as ...

. The reaction scheme is as follows: The ketone or aldehyde is activated by conversion to cyclic

by reaction with a dithiol (

nucleophilic substitution In chemistry, a nucleophilic substitution is a class of chemical reaction A chemical reaction is a process that leads to the chemical transformation of one set of chemical substances to another. Classically, chemical reactions encompass c ...

) 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 Nickel sulfide is any inorganic compound with the formula NiSx. They range in color from bronze (Ni3S2) to black (NiS2). The nickel sulfide with simplest stoichiometry is NiS, also known as the mineral millerite. From the economic perspective, ...

. 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 group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the res ...

History

The reaction is named after Ralph Mozingo, who reported the cleavage of

thioether In organic chemistry, an organic sulfide (British English sulphide) or thioether is an organosulfur functional group with the connectivity as shown on right. Like many other sulfur-containing compounds, volatile sulfides have foul odors. A sul ...

s with Raney nickel in 1942. However the modern iteration of the reaction, involving the cyclic dithioacetal, was developed by

Melville Wolfrom Melville Lawrence Wolfrom (April 2, 1900 – June 20, 1969) was an American chemist. Early life, education, and career Melville Wolfrom's grandfather Johann Lorenz Wolfrum immigrated to the United States from Aš in 1854, and was of Sudeten Germ ...

References

{{Reflist, 2 Organic reduction reactions Organic redox reactions Name reactions