Doctoral Dissertations
Date of Award
12-2002
Degree Type
Dissertation
Degree Name
Doctor of Philosophy
Major
Chemistry
Major Professor
Jamie L. Adcock
Committee Members
Bob Compton, Lee Magrid, David Brian
Abstract
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.
Recommended Citation
Smith, Kenneth, "The synthesis and reactions of substituted perfluoroadamantanes, fluorofullerenes and norbornane carbocations. " PhD diss., University of Tennessee, 2002.
https://trace.tennessee.edu/utk_graddiss/6311