Publication Date

2014

Document Type

Dissertation/Thesis

First Advisor

Adler, Marc Jordan, 1981-

Degree Name

Ph.D. (Doctor of Philosophy)

Legacy Department

Department of Chemistry and Biochemistry

LCSH

Lewis acids; Organic compounds--Synthesis; Analytical chemistry; Inorganic chemistry; Organic chemistry

Abstract

Lewis acids have been a cornerstone in modern organic synthesis, but the use of silicon Lewis acids has not received as much attention. Silicon Lewis acids have unique features that differ from some typical metal catalysts. Some of these properties include good solubility in organic solvents, decreased likelihood for ligand exchange, and decreased toxicity. These differences make the use of silicon Lewis acids a versatile tool for organic synthesis. There is a great deal yet to explore about silicon Lewis acidity and silicon Lewis acids and from that two main projects arose in order to further study these concepts.||Preparation of a small library of silyloxybenzaldehydes allowed for the design of a chemical probe to investigate if the groups have any influence on the neighboring carbonyl group. The most common use for silicon in organic chemistry is where some trialkyl silicon moiety serves as a protecting group. This probe looks to rethink the current silicon protecting group archetype. Taking concepts learned from this chemical probe and from literature it is proposed that a novel silicon Lewis acid scaffold can be constructed. This silicon Lewis acid scaffold would be easily modifiable and tunable and have great potential on future catalyst design.

Comments

Advisors: Marc J. Adler.||Committee members: Sherine Elsawa; Tim J. Hagen; Narayan S. Hosmane; Douglas A. Klumpp.

Extent

219 pages

Language

eng

Publisher

Northern Illinois University

Rights Statement

In Copyright

Rights Statement 2

NIU theses are protected by copyright. They may be viewed from Huskie Commons for any purpose, but reproduction or distribution in any format is prohibited without the written permission of the authors.

Media Type

Text

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