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The Reactivity Of Potassium Carbanions With Epoxides, Christina Dorado

Open Access Theses & Dissertations

The reaction of &alpha-cumylpotassium and cyclohexene oxide produces trans-cumylcyclohexanol in high yield in the presence of excess cumene. Reactions of 1.1 and 2.0 equivalents of cumene with one equivalent of n-butylpotassium to make &alpha-cumylpotassium were shown to take several days to reach a maximum yield in the subsequent reaction of &alpha-cumylpotassium and cyclohexene oxide. Although it was initially hypothesized that the high yield was attributed to the interaction of the potassium with the aromatic rings of the &alpha-cumyl anion and the excess cumene, which was confirmed by molecular modeling studies, these reactions demonstrated that no large excess of …