Publication Date
2019
Document Type
Dissertation/Thesis
First Advisor
Klumpp, Douglas A.
Degree Name
Ph.D. (Doctor of Philosophy)
Legacy Department
Department of Chemistry and Biochemistry
Abstract
The work outlined in this dissertation describes the development of synthetic methodologies utilizing a wide electrophilicity range of substrates towards the synthesis of new compounds. Substitution, addition, and superelectrophilic chemistry are powerful tools to afford potentially important compounds. These concepts are summarized in chapter 1.
Chapter 2 describes the capture of superacid catalyzed fluorenyl cations with nitriles (Ritter reaction) and alcohols. Optimization of reaction conditions and extensive scope studies were performed.
In chapter 3, the Michael addition of organometallic reagents with N-heterocyclic substituted olefins is explored. The nucleophilic carbanion intermediate species is shown to have reactivity towards strong electrophiles. With this chemistry, two new C-C bonds are formed, an uncommon feature of the Michael reaction.
In chapter 4, the synthesis of potential flavor compounds and cooling agents is described. Synthetic procedure and workup are deemed vital for yield and purity of such compounds.
Recommended Citation
Stentzel, Michael R., "Development of Synthetic Methodologies of Nucleophile-Electrophile Chemistry" (2019). Graduate Research Theses & Dissertations. 7699.
https://huskiecommons.lib.niu.edu/allgraduate-thesesdissertations/7699
Extent
248 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
