Wolff-Kishner Reduction; Huang-Minlon Modification

N. Kishner, J. Russ. Phys. Chem. Soc. 43, 582 (1911), C.A. 6, 347 (1912); L. Wolff, Ann. 394, 86 (1912); Huang-Minlon, J. Am. Chem. Soc. 68, 2487 (1946).

Complete reduction of carbonyl compounds to methyl or methylene groups on heating with hydrazine hydrate and a base. In the Huang-Minlon modification diethylene glycol is used as a solvent:

Reviews: D. Todd, Org. React. 4, 378 (1948); H. H. Szmant, Angew. Chem. Int. Ed. 7, 120 (1968); F. Asinger, H. H. Vogel, Houben-Weyl 5/1a, 251, 456 (1970); H. Balli, ibid. 5/1b, 629 (1972); R. O. Hutchins, M. K. Hutchins, Comp. Org. Syn. 8, 327-343 (1991). Bond cleavage: R. P. Lemieux, P. Beak, Tetrahedron Letters 30, 1353 (1989). Synthetic application: A. Srikrishna, D. Vijaykumuv, J. Chem. Soc. Perkin Trans. I 1999, 1265. Cf. Clemmensen Reduction; Haworth Phenanthrene Synthesis.