Degree Type

Dissertation

Date of Award

1991

Degree Name

Doctor of Philosophy

Department

Chemistry

First Advisor

George A. Kraus

Abstract

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.

DOI

https://doi.org/10.31274/rtd-180813-9497

Publisher

Digital Repository @ Iowa State University, http://lib.dr.iastate.edu/

Copyright Owner

Jeffrey Alan Hansen

Language

en

Proquest ID

AAI9202359

File Format

application/pdf

File Size

73 pages

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