REDUCTION OF CYCLIC ALKENES AND KETONES VIA TRANSFER HYDROGENATION USING WILKINSON'S CATALYST AND ISOPROPANOL

摘要

Unsaturated organic compounds, such as alkenes or those containing a carbonyl group, are conventionally reduced using hydrogen gas and a transition metal catalyst. In hydrogen-transfer catalysis, the unsaturated organic compound can be reduced without using an external source of H2 gas. In this paper, Wilkinson's catalyst, [RhCI(PPh3)3], was used as a hydrogen-transfer catalyst along with isopropanol as a hydrogen-transfer agent to successfully reduce a series of cyclic alkenes and ketones. Cyclohexanone was reduced to cyclohexanol and cyclohexene to cyclohexane. In addition, cyclooctene and 1,5-cyclooctadiene were both converted to cyclooctane. The formation of acetone, which was produced when hydrogen was removed from the isopropanol hydrogen-transfer agent, was monitored using infrared spectroscopy and the products confirmed via gas chromatography.