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Homogeneous hydrogenations ofα, β-unsaturated compounds using pentacyanocobaltate (II) anion as catalyst system

  • G S R Subba Rao
  • J Rajaram
  • S Rathnamala
  • R Sivaramakrishnan
Article

Abstract

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.

Keywords

Homogeneous hydrogenation pentacyanocobaltate (II) α, β-unsaturated ketones 

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Copyright information

© Indian Academy of Sciences 1977

Authors and Affiliations

  • G S R Subba Rao
    • 1
  • J Rajaram
    • 1
  • S Rathnamala
    • 1
  • R Sivaramakrishnan
    • 1
  1. 1.Department of Organic ChemistryIndian Institute of ScienceBangalore

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