Date of Award
Doctor of Philosophy
George A. Kraus
Bridgehead intermediates have only recently been employed in organic synthesis. This study was undertaken to further explore and broaden their usefulness. Reaction of 9-oxabicyclo(3.3.1) octane mesylates with Lewis acids gave bridgehead oxonium ions which could be reacted with substituted benzenes. Bridgehead sulfoxides were reacted under a variety of conditions to provide bridgehead intermediates. Thermal conditions gave a bridgehead enone that underwent an interesting rearrangement. Reaction with trifluoroacetic anhydride provided the first example of a bridgehead Pummerer reaction. Base promoted elimination afforded a bridgehead enone which was trapped by ammonia.
Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/
Jeffrey Alan Hansen
Hansen, Jeffrey Alan, "The utilization of bridgehead intermediates in organic synthesis " (1991). Retrospective Theses and Dissertations. 10038.