Publication Date

Spring 2017

Advisor(s) - Committee Chair

Dr. D.W. Slocum (Director), Dr. Rui Zhang, and Dr. Kevin Williams

Degree Program

Department of Chemistry

Degree Type

Master of Science

Abstract

The halogenated derivatives of heterocyclic compounds (haloarenes) are highly utilized in many fields of chemistry, including drug discovery, medicinal, and material chemistry. There are a variety of ways to functionalize an aromatic system and introduce halogen substituent into the ring. However, electrophilic aromatic substitution (EAS) has been the focus of growing attention, particularly for electronrich substrates.

Electrophilic aromatic bromination protocols are one of the most important electrophilic aromatic substitution reactions. However, preparation of bromoarenes classically recommends the use of highly oxidative agents along with utilizing various metal catalysts in a halogenated solvent. The corrosive and toxic nature of these reagents and need of harsh conditions for these protocols make their utility less desirable in current practice. Furthermore, lack of regioselectivity for most substituted aromatics is the other distinguished drawback, since most products contain ortho/para directors which afford a mixture of isomers.

The innovation of our procedure for the bromination of various substituted aromatic compounds is twofold in that highly regiospecific para-bromination of activated aryls by treatment with NBS has been accomplished. Although various reaction mediums, such as cyclohexane, acetone, and acetonitrile has been used in this procedure, the significant high yields of the product formation along with the very short reaction times using acetonitrile make this approach more attractive. That this regiospecific p-substitution takes place under such mild conditions leads us to question whether it is EAS.

Disciplines

Organic Chemistry | Physical Chemistry

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