Main content

A platform upgrade will be performed on the Atrium Institutional Repository from Monday, July 13 to Wenesday, July 15, 2020 (inclusive). During this time, users will not be able to submit new items to the Atrium. Users will still be able to browse, view, and download items that are already available in the Atrium. We apologize for any inconvenience this may cause.

Inter- and Intramolecular Ring-Opening Reactions of Oxabicyclic Substrates.

Show full item record

Title: Inter- and Intramolecular Ring-Opening Reactions of Oxabicyclic Substrates.
Author: Wicks, Christopher
Department: Department of Chemistry
Program: Chemistry
Advisor: Tam, William
Abstract: Oxabenzonorbornadiene (OBD) and derivatives thereof have become key substrates of interest within synthetic organic chemistry and natural product synthesis as they enable the formation of multiple stereocenters in a single transformation. The present work expands on previous studies to investigate various intramolecular transformations, and regiochemical implications regarding ring-opening reactions of asymmetric oxabicyclic alkenes. Acid-catalyzed intramolecular ring-opening reactions of cyclopropanated oxabenzonorbornadiene (CPOBD) derivatives were investigated to afford novel medium-sized ring systems in moderate to good yields and good to excellent regioselectivity. Similarly, a Ni catalyzed intramolecular ring-opening reaction of alkyl halide tethered OBD compounds was optimized, thus generating a naphthalene derivative in excellent yields. Lastly, iridium-catalyzed ring-opening reactions of unsymmetrical C1-substituted OBD derivatives is presented using alcohols and water as nucleophiles which allows for the selective synthesis of previously inaccessible substrates.
Date: 2019-08
Terms of Use: All items in the Atrium are protected by copyright with all rights reserved unless otherwise indicated.

Files in this item

Files Size Format View
Wicks_Christopher_201908_MSc.pdfuntranslated 4.183Mb PDF View/Open

This item appears in the following Collection(s)

Show full item record