The synthesis and reactions of substituted perfluoroadamantanes, fluorofullerenes and norbornane carbocations

Fluoro and trifluoromethyl groups are becoming increasingly popular in pharmaceuticals, as their inductive effects can be used to tailor a drug's specific interactions. Fluorous syntheses are also now becoming commonplace due to the efficient partitioning possible between fluorous and organic phases. Several new F-adamantyl derivatives were synthesized from F-Adamantyl lithium as targets for future incorporation into pharmaceuticals or for use as fluorous tags. They are: Ethyl-F-Adamantane from ethyl iodide, methyl Fadamantyl ketone and enolate from acetyl chloride, and TIPS protected F-Adamantyl ethanol from TIPS protected 2-bromoethanol. The synthesis of F-adamantyl sulfonyl halides was attempted, however, the F-adamantyl anion attacks the chlorine of sulfonyl chloride fluoride rather than the sulfur in an SNX reaction. Also, F-adamantyl sulfonyl bromide formed by the reaction ofF-Adamantyl Lithium with sulfur dioxide and bromine desulfonylated to form Fadamantyl bromide.