Synthesis 2010(3): 421-424  
DOI: 10.1055/s-0029-1217117
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Hydrogenation of α,β-Unsaturated Ketones over Wilkinson’s Catalyst

Johannes H. van Tondera, Charlene Maraisa, David J. Cole-Hamiltonb, Barend C. B. Bezuidenhoudt*a
a Department of Chemistry, University of the Free State, PO Box 339, Bloemfontein 9300, South Africa
Fax: +27(51)4446384; e-Mail: bezuidbc.sci@ufs.ac.za;
b School of Chemistry, University of St Andrews, St Andrews, Fife, KY16 9ST, UK
Further Information

Publication History

Received 6 October 2009
Publication Date:
13 November 2009 (online)

Abstract

The reactivity of a variety of α,β-unsaturated acyclic and cyclic ketones towards regioselective hydrogenation in the presence of Wilkinson’s catalyst was determined. Hydrogenation of sterically hindered α,β-unsaturated ketones proceeded at inefficient rates, if at all.

4

As the nonvolatile substrates were solids, they had to be dissolved in solvent, which necessitated the use of the larger reactor for better mass transfer.