Electronic Thesis and Dissertation Repository


Master of Science




Brian L. Pagenkopf


Cyclopropane 1,1-diesters have been investigated as a source of donor-acceptor cyclopropanes, providing an understanding of the mechanism of reaction between these cyclopropanes and nitrosoarenes, as well as azo dicarboxylates. Cross-over experiments have been utilized to provide key pieces of experimental evidence that help generate a theoretical model of the reactions. By understanding these reactions with precision, the avenue to expand the reaction scope and develop other useful reactions is opened up. This allows the chemistry to be better utilized, providing easier access to important molecules when needed, and contributes to advancing the field of synthetic organic chemistry.

In addition, cyclobutane 1,1-diesters were also investigated as a source of donor-acceptor cyclobutanes. Specifically, their use in cycloaddition reactions has been developed to include the reaction of cyclobutanes with cis-diazenes, providing access to hexahydropyridazines. These compounds are synthesized in an efficient manner and are known to contain biologically active properties.