113 The Reactivity of Organo-Potassium in Nucleophilic Reactions

Wednesday, November 4, 2009: 8:40 AM
Rio Grande (Camino Real Hotel)
Christina Alvarado , Department of Chemistry, University of Texas at El Paso, El Paso, TX
James Salvador , Chemistry, University of Texas at El Paso, El Paso, TX
Lithium and Magnesium are two elements that have been studied extensively in the field of organic chemistry. Potassium, an element that undergoes similar chemistry to that of Lithium and Magnesium, is not studied as extensively due to its high reactivity and instability in its elemental state. Potassium exhibits not only the ability to undergo similar chemistry to that of Lithium and Magnesium but it also shows the potential of undergoing reactions that its more popular counterparts cannot. In particular, the reaction of cyclohexene oxide, a secondary epoxide, with alpha-cumyl potassium in order to yield trans-cumyl cyclohexanol was successful, where as organo-lithium and magnesium species were not capable of such a sterically hindered reaction. In this research project, we propose to study the solvent effect on organo-potassium species, particularly that of alpha-cumyl potassium. We predict that the presence of pi-interactions between aromatic solvents and our alpha-cumyl potassium increases the yield of the reaction by breaking up organo-potassium oligomers. We propose to study different reaction conditions in which we have primary, secondary and tertiary alkyl potassium species reacting with different carbon electrophiles. Finally, we propose to identify different potassium salts that can be used in the potassium-lithium exchange reaction to produce our alkyl-potassium species.
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