Date of Award

1-1-2016

Document Type

Dissertation

Degree Name

Ph.D.

Organizational Unit

Chemistry and Biochemistry

First Advisor

Andrei Kutateladze, Ph.D.

Second Advisor

James Fogelman, Ph.D.

Third Advisor

Bryan Cowen

Fourth Advisor

Brian Michel

Keywords

Beta-lactams, Diversity oriented synthesis, Hydantoins, O-azaxylylenes, Photochemistry, Polyheterocycles

Abstract

This research set out to continue the exploration and diversification of excited state o-azaxylylene cycloadditions, utilizing both pre-photochemical and post-photochemical modifications.

Pre-photochemical modifications came through the addition of heteroatoms, namely nitrogen and oxygen, to the tether that links the unsaturated photopendant to the photogenerated o-azaxylylene. Photochemistry resulted in the formation of new, interesting N, O, S polyheterocycles.

Post-photochemical modifications took place through several different cycloaddition reactions, including a [4+2] hetero-Diels Alder reaction, a [4+2] Povarov cyclization, a [3+2] nitrile oxide addition, and a [3+2] nitrone cyclization. These reactions were applied first to a model system, and then to a new scaffold that contained the biologically relevant beta-lactam fragment.

A summation of engineering work is also included to detail the development and implementation of several new LED irradiators. These irradiators are key to the photochemistry that will be discussed, and their development will serve as a blueprint for future work and improvement.

Publication Statement

Copyright is held by the author. User is responsible for all copyright compliance.

Rights Holder

Weston James Umstead

Provenance

Received from ProQuest

File Format

application/pdf

Language

en

File Size

123 p.

Discipline

Organic Chemistry

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