The synthesis and reactivity of 3-amino and 3-oxycyclopentadienones
Publisher
The University of Arizona.Rights
Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author.Abstract
[2+2+1] iron and cobalt mediated cycloadditions have been applied towards the synthesis of 3-amino and 3-oxycyclopentadienones. These methods have provided an efficient means of generating [3.3.0], [4.3.0], and [5.3.0] bicyclic-cyclopentadienone ring systems. In an effort to probe the reactivity of our metal complexed dienones, we proceeded to subject them to cycloaddition reactions. With this goal in mind, we applied oxidative demetallation conditions to provide the metal free bicyclic-cyclopentadienones. Cycloaddition of the bicyclic-dienones with a number of pi donors and acceptors provided chemo and regioselective cycloadducts in an efficient fashion. Final studies included investigations of the iron cyclopentadienones in diastereoselective reactions.Type
textDissertation-Reproduction (electronic)
Degree Name
Ph.D.Degree Level
doctoralDegree Program
Graduate CollegeChemistry