Main content

Investigations into the Ruthenium Catalyzed Ring Opening and Dimerization Reactions of Oxabicyclic Alkenes

Show full item record

Title: Investigations into the Ruthenium Catalyzed Ring Opening and Dimerization Reactions of Oxabicyclic Alkenes
Author: Jack, Kelsey
Department: Department of Chemistry
Program: Chemistry
Advisor: Tam, William
Abstract: Oxabicyclic alkenes have been the focus of many synthetic studies as they are versatile compounds which act as synthetic intermediates to produce a variety of useful heterocyclic, carbocyclic and acyclic products. The nucleophilic ring opening reaction of oxabenzonorbornadiene was studied. Methanol was the primary nucleophile used throughout the investigation, however various other alcohol nucleophiles were also tested for their efficacy. The effects of substitution were explored, providing ring opened products in yields of up to 81%. The [2+2] cyclodimerization reaction of oxanorbornadienes was also examined providing the first examples of dimers of this kind. The scope was expanded to include other 2,3-diester oxanorbornadienes as well as various C1 substitutions. Changing the ester moiety did not affect the reaction, however the addition of a C1 alkyl substituent did result in lower yields. Moderate yields of up to 66% were obtained. Additionally, a new ruthenium complex was discovered in the process.
URI: http://hdl.handle.net/10214/4738
Date: 2012-12


Files in this item

Files Size Format View
Jack_Kelsey_201212_MSc.pdf 3.414Mb PDF View/Open

This item appears in the following Collection(s)

Show full item record