REDUCING UNSATURATED ORGANIC COMPOUNDS VIA TRANSFER HYDROGENATION USING WILKINSON'S CATALYST AND ISOPROPANOL

摘要

The reduction of unsaturated organic substrates, such as alkenes or carbonyl containing compounds, is conventionally performed using hydrogen gas and a transition metal catalyst. In catalytic transfer hydrogenation, hydrogen is added to an unsaturated organic compound without using gaseous H2. In the reactions described in this paper, isopropanol was employed as the hydrogen transfer agent, which, upon removal of hydrogen, was converted to acetone. Wilkinson's catalyst [RhCI(PPh3)3] was used as the hydrogen transfer catalyst to successfully reduce organic compounds containing C=C and C=0 bonds. Using this method, the ketones acetophenone and benzophenone were successfully reduced to the secondary alcohols 1-phenylethanol and diphenylmethanol respectively. In addition, an alkene (1-hexane) was saturated to an alkane (hexane) and 5-hexen-2-one, a compound containing both C=C and C=0 bonds, was converted to 2-hexanol. The formation of acetone, produced when hydrogen was removed from the isopropanol hydrogen transfer agent, was monitored using infrared spectroscopy and the products confirmed via gas chromatography where relevant.