Presentation Title

Synthesis and Lithiation of toluene tricarbonyl chromium

Format of Presentation

Poster to be presented the Friday of the conference

Presenter Information

Max K. IrlFollow

Abstract

Toluene tricarbonyl chromium was prepared by microwave reaction of hexacarbonyl chromium with toluene in THF followed by purification and characterization of the complex. The tricarbonyl chromium complex then underwent benzylic lithiation under kinetic conditions. This procedure was optimized and wheras the standard procedure involves lithiation with an advance prepared lithium amine, this lithiation was done directly with tertiary butyl lithium. In it's original characterization it was then quenched with trimethylsilyl chloroide Then the toluene tricarbonyl chromium was then lithiated once more, and quenched with diethylcarbonic chloride. This allowed for the further lithiation the produced diethyl-2-phenylacetamide was lithiated in the presence of a chiral lithiating agen (sparteine) to generate a chiral carbon, and non racemic mixture.

Department

Chemistry

Faculty Advisor

Norman Reed

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Synthesis and Lithiation of toluene tricarbonyl chromium

Toluene tricarbonyl chromium was prepared by microwave reaction of hexacarbonyl chromium with toluene in THF followed by purification and characterization of the complex. The tricarbonyl chromium complex then underwent benzylic lithiation under kinetic conditions. This procedure was optimized and wheras the standard procedure involves lithiation with an advance prepared lithium amine, this lithiation was done directly with tertiary butyl lithium. In it's original characterization it was then quenched with trimethylsilyl chloroide Then the toluene tricarbonyl chromium was then lithiated once more, and quenched with diethylcarbonic chloride. This allowed for the further lithiation the produced diethyl-2-phenylacetamide was lithiated in the presence of a chiral lithiating agen (sparteine) to generate a chiral carbon, and non racemic mixture.