Homogeneous hydrogenations ofα, β-unsaturated compounds using pentacyanocobaltate (II) anion as catalyst system
- 41 Downloads
Hydrogenation of someα, β-unsaturated carbonyl compounds using potassium pentacyanocobaltate (II), K3Co(CN)5, as a homogeneous catalyst has been investigated. Thus, hydrogenation of 1-carvone (I), mesityl oxide (4), 2-cyclohexenone (8) and benzalacetone (6) afforded the corresponding dihydrocompounds. Hydrogenation ofβ-ionone (10) afforded a mixture of theα, β-dihydrocompounds (14) and (15). In all these cases, it was observed that the reaction proceeded to completion only in the presence of added base. Hydrogenation of 5α-androst-l-en-17β-ol-3-one acetate (19) afforded the saturated compound, 5α-androst-17β-ol-3-one (20) in 60% yield. It was found that other steroid enones and dienones were not reduced by this catalyst system.
KeywordsHomogeneous hydrogenation pentacyanocobaltate (II) α, β-unsaturated ketones
Unable to display preview. Download preview PDF.
- Birch A J and Williamson D H 1976Organic Reactions Vol. 24 p 1–186Google Scholar
- Birch A J and Walker K A M 1966J. Chem. Soc. (C) 1894Google Scholar
- Butenandt A and Dannenburg H 1940Chem. Ber. 73 206Google Scholar
- Kwiatek J, Mador I L and Seyler J K 1963Advances in Chemistry Vol 37 (American Chemical Society, Washington D. C.) 201Google Scholar
- Kwiatek J and Seyler J K 1968Advances in Chemistry Vol 70 (American Chemical Society, Washington D.C.) 207Google Scholar
- Miki T and Hara Y 1956Pharm. Bull. (Japan) 4 85Google Scholar