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 breaking ...

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 b ...

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 gro ...

to the corresponding

alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in wh ...

via a dithioacetal. The reaction scheme is as follows: The ketone or aldehyde is activated by conversion to cyclic dithioacetal by reaction with a dithiol (

nucleophilic substitution In chemistry, a nucleophilic substitution is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The ...

) 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 Clemmensen is a surname. Notable people with the surname include: *Andrew Clemmensen, member of Short Stack, an Australian rock band * Charlotte Clemmensen (born 1992), Danish curler * Ejgil Clemmensen (1890–1932), Danish rower who competed in th ...

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 r ...

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 su ...

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

References

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