The synthesis and reactivity of 3-amino and 3-oxycyclopentadienones

[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.

Name thesis:degree_name

Ph.D.

Level thesis:degree_level

doctoral

Discipline thesis:degree_discipline

Graduate College

Grantor dc:publisher

The University of Arizona.

Year dc:date.issued

2002

Author dc:creator

• Imbriglio, Jason

Advisor dc:contributor.advisor

• Rainier, Jon D.

• Chemistry, Organic.

Statement dc: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.

Language dc:language.iso

en_US

Handle dc:identifier.uri

http://hdl.handle.net/10150/289769

OAI identifier oai:identifier

oai:repository.arizona.edu:10150/289769