Main content

Exploring the New Chemistry of 3-Aza-2-oxabicyclo[2.2.1]hept-5-enes

Show simple item record

dc.contributor.advisor Tam, William
dc.contributor.author Tait, Katrina Marie
dc.date.accessioned 2018-01-11T20:12:52Z
dc.date.available 2018-01-11T20:12:52Z
dc.date.copyright 2018-01
dc.date.created 2018-01-10
dc.date.issued 2018-01-11
dc.identifier.uri http://hdl.handle.net/10214/12177
dc.description.abstract Synthetic organic chemistry is at the center of drug design/development, which uses literature reactions to create biologically active compounds. A downfall to this approach is that there is still so much unknown about the reactivity profile of organic bicyclic molecules. While many heterobicyclic alkenes have been studied, there are significantly fewer reports about the reactivity of 3-aza-2-oxabicyclo[2.2.1]hept-5-enes. The first part of this work examines the Lewis acid-catalyzed ring-opening/rearrangement of 3-aza-2-oxabicyclo[2.2.1]hept-5-enes to form a cyclized nitrone or oxazolidinone product depending on the catalyst. The next section investigates the ruthenium-catalyzed ring-opening and isomerization of 3-aza-2-oxabicylo[2.2.1]hept-5-enes in the presence of amines. Ruthenium mediates the ring-opening to form an unsaturated aminocyclopentenol product which undergoes allylic alcohol isomerization to provide the corresponding cyclopentanone. The final section first investigates the cyclopropanation of 3-aza-2-oxabicyclo[2.2.1]hept-5-enes under palladium catalysis with diazomethane which was well tolerated for various substrates. The latter part of this section focuses on the acid-catalyzed nucleophilic ring-opening reaction of the previously synthesized cyclopropanated substrate with alcohols. The substrate undergoes ring-opening through C-O bond cleavage to form a substituted methanocyclopentane product. en_US
dc.description.sponsorship NSERC (Natural Sciences and Engineering Research Council of Canada) en_US
dc.language.iso en en_US
dc.rights Attribution-NoDerivs 2.5 Canada *
dc.rights.uri http://creativecommons.org/licenses/by-nd/2.5/ca/ *
dc.subject heterobicyclic alkene en_US
dc.subject ring-opening en_US
dc.subject Lewis acid en_US
dc.subject cyclopropanation en_US
dc.subject transition metal en_US
dc.title Exploring the New Chemistry of 3-Aza-2-oxabicyclo[2.2.1]hept-5-enes en_US
dc.type Thesis en_US
dc.degree.programme Chemistry en_US
dc.degree.name Master of Science en_US
dc.degree.department Department of Chemistry en_US
dc.rights.license All items in the Atrium are protected by copyright with all rights reserved unless otherwise indicated.


Files in this item

Files Size Format View Description
Tait_Katrina_201801_Msc.pdf.pdf 5.981Mb PDF View/Open Katrina Marie Tait full thesis

This item appears in the following Collection(s)

Show simple item record

Attribution-NoDerivs 2.5 Canada Except where otherwise noted, this item's license is described as Attribution-NoDerivs 2.5 Canada