Master of Science
Dr. M.A. Kerr
Previous work in the Kerr group has shown the success of donor-acceptor cyclopropanes as substrates in a variety of synthetic reactions; this document will apply the use of donor acceptor cyclopropanes in various synthetic reactions. This was done using a 2-substituted 1,1-cyclopropanediester, in the Overman Rearrangement, which has yet to be explored using DA cyclopropanes. Another useful DA cyclopropane is the novel acetylene-bearing donor acceptor diester cyclopropanes which would be synthetically useful in a wide variety of reactions. In particular, the Conia-ene cyclization occurred intramolecularly with this alkyne DA cyclopropane with a large library of nucleophiles. Finally, taking this acetylene-bearing DA cyclopropane, it was converted to the hemimalonate version, and subjected to a ring-opening by azide as the nucleophile to generate an alkyl azide; which then underwent a [3+2] dipolar cycloaddition with the alkyne to form novel linearly fused tricyclic triazoles.
Flisar, Michelle E., "The Application of Novel Donor Acceptor Cyclopropanes in the Synthesis of Linearly Fused Tricyclic Triazoles" (2014). Electronic Thesis and Dissertation Repository. 2352.