Title:

Functionalizing Adamantane with Unconventional Leaving Groups

Adamantane is a rigid hydrocarbon cage that forms an unusually stable carbocation. By utilizing this stable carbocation, it is possible to attach various leaving groups with different ionization rates to its tertiary carbon atoms. Then, by multiple nucleophilic substitution reactions, adamantane can be functionalized on demand with four unique functional groups. In order to achieve a uniquely functionalized adamantane, suitable leaving groups must be determined first. After various tests to attach commonly thought of leaving groups, it was discovered that conventional leaving groups had ionization rates that were too high, thus leading to the generation of adamantanol as a final product instead of the desired compound. It was determined that leaving groups with lower rates of ionization worked best, including chloro- and bromo- groups. Unconventional leaving groups also performed well and show promise toward achieving the end goal of a uniquely functionalized adamantane derivative.

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