Publication Date


Document Type


First Advisor

Klumpp, Douglas A.

Degree Name

Ph.D. (Doctor of Philosophy)

Legacy Department

Department of Chemistry and Biochemistry


Chemistry; Organic chemistry


This dissertation describes the use of triflic acid as catalyst for generating reactive intermediates and studying their reactivities under varying reaction conditions. The first chapter is an introduction to the types of organic reactions and acids. This chapter also discusses generation and reactivities of superelectrophiles as well. Chapter 2 discusses the synthesis of 3,3-disubstituted-2-oxindoles from the reaction of a series of acetonyl-substituted 3-hydroxy-2-oxindoles with arene in the presence of triflic acid. These reactions are performed under mild conditions and products isolated in decent yields. In chapter 3, the effects of charge migration in a tetra- and pentacationic superelectrophile is studied. These highly reactive intermediates are reacted with benzene at elevated temperatures. In the absence of benzene, cyclization occurs to produce novel N-heterocyclic compounds. Alcohol precursors are also ionized to generate these reactive intermediates and studied using low-temperature NMR. Chapter 4 talks about the effects of charge-charge repulsion on the aromaticity and anti-aromaticity in fluorenyl and dibenzosuberenyl cations respectively. These cations are generated from ionization of the respective biaryl ketones and dibenzosuberenols with superacid. With increasing charge, there is a corresponding increase in the aromaticity or anti-aromaticity of the respective system. Chapter 5 describes the superacid-promoted synthesis of heterocycle-containing 9,9-diarylfluorenes from biaryl ketones. Products are generally isolated in good yields using mild reaction conditions. Some of these compounds are used in the manufacture of organic light emitting diodes (OLEDs) and other organic-based electronics.


Advisors: Douglas A. Klumpp.||Committee members: Dennis Brown; Timothy J. Hagen; Narayan S. Hosmane; Lee S. Sunderlin.||Includes bibliographical references.||Includes illustrations.


xvi, 318 pages




Northern Illinois University

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