Electronic Thesis and Dissertation Repository

Degree

Master of Science

Program

Chemistry

Supervisor

Dr. M.A. Kerr

Abstract

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.


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