Wolff-Kishner Reduction

Definition:

Complete reduction of carbonyl compounds to methyl or methylene groups on heating with hydrazine hydrate and base.

Frequency of appearance:

        This bar graph represents all of the online articles that were found to contain this specific name reaction in the title of the article. Tetrahedron letters, Tetrahedron, Synthetic letters, Synthesis, Journal of Organic Chemistry and Journal of the American Chemical Society are represented here. This table by no means represents the periodicity of the name reaction found in the literature.

Original Reference:

1. Kishner, N.J. Russ. Phys. Chem. Soc., 43, 582 (1911).
2. Wolff, L. Ann., 1912, 394, 86.
3. Huang-Minlon J. Am. Chem. Soc., 1949, 71, 3301.

Recent academic references: Click here for more references

4. Structure-Activity Relationships for the Antileishmanial and Antitrypanosomal Activities of 1'-Substituted 9-Anilinoacridines

• Gamage, S. A., et al., J. Med. Chem.; 1997; 40(16); 2634-2642.

5. First diastereoselective synthesis of (-)-thrysiflorin a methyl ester

• Abad, A.; Agulló, C.; Arnó, M.; Marín; M.L.; Zarazozá, R.J.* SynLett, 1997, 574-576.

6. http://www.arkat.org/arkat/journal/Govi/Govi5.pdf

Recent process references:

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Mechanism:

Scope and Limitations:

• Very high temperatures employed (200 C). ^B
• Yields are often below 70% due to elimination or isomerization side products. ^B
• Modifications of this reaction include the Huang-Minlon Modification (reflux) and a alkoxy base-DMSO (room temp). ^{A+ B}
• Clemmensen (acidic) reduction is complementary to the Wolff (basic) reduction. ^A

Synonyms: