Thioketal reduction
The thioketal-reduction is a reaction of organic chemistry , in the thioketals to alkane reduces be. In this way, ketones or aldehydes can also be reduced to alkane under mild conditions. The reaction is also called the Mozingo reaction or Mozingo reduction or Wolfrom-Karabinos method .
Naming
Ralph Mozingo laid the foundation for thioketal reduction in 1943 with a paper on the hydrogenolysis of thio compounds. The reduction of thioketals is therefore often called the Mozingo reaction, although this method is not limited to thioketals, but rather generally describes desulphurisation by Raney nickel . Wolfrom and Karabinos recognized the potential of this reaction in 1944 and extended its application to thioketals as well.
Overview reaction
A thioketal is refluxed with Raney nickel in ethanol , resulting in the corresponding alkane. This is often done with the addition of hydrogen, but this is not always necessary.
Potential and criticism
The thioketal reduction is an alternative to the Wolff-Kishner reduction , which requires basic conditions and to the Clemmensen reduction which takes place in acid . However, the problem is that the thioketal has to be synthesized in an additional step. In addition, Raney nickel is pyrophoric .
Individual evidence
- Jump up ↑ Ralph Mozingo, Donald E. Wolf, Stanton A. Harris, Karl Folkers: Hydrogenolysis of Sulfur Compounds by Raney Nickel Catalyst . In: Journal of the American Chemical Society . tape 65 , no. 6 , June 1943, p. 1013-1016 , doi : 10.1021 / ja01246a005 .
- ↑ a b Jana Rentner, Marko Kljajic, Lisa Offner, Rolf Breinbauer: Recent advances and applications of reductive desulfurization in organic synthesis . In: Tetrahedron . tape 70 , no. 47 , November 2014, p. 8983-9027 , doi : 10.1016 / j.tet.2014.06.104 .
- ↑ ML Wolfrom, JV Karabinos: carbonyl reduction by thioacetal hydrogenolysis . In: Journal of the American Chemical Society . tape 66 , no. 6 , June 1944, p. 909-911 , doi : 10.1021 / ja01234a021 .