The Synthesis of Naphthalene-Containing Compounds and Materials Using Benzannulation Reactions

Hein, Samuel Jay

The Synthesis of Naphthalene-Containing Compounds and Materials Using Benzannulation Reactions

Abstract

This dissertation describes recent advances in methodology to access novel aromatic architectures using a benzannulation strategy (Chapter 1). Silyl protected acetylenes are readily reacted to yield the corresponding 2-naphthylsilane. These compounds serve as synthetically useful building blocks for further derivatization and iterative benzannulation to access sterically crowded substrates (Chapter 2). Despite the high efficiency of this reaction, phenylene ethynylene macrocycles prove to be too rigid to undergo complete benzannulation (Chapter 3). Finally, the scope of this transformation was expanded beyond aryl substituted acetylenes with the benzannulation of silyl-haloacetylenes (Chapter 4). These products readily generate 2-naphthynes with the addition of cesium fluoride and can be oligomerized or cyclized to isolate substituted ortho-naphthalenes. Through our fundamental studies into this transformation, we have shown it serves as a versatile reaction in the organic synthetic chemists toolbox to access novel aromatic architectures.

Date Issued

2017-05-30

Keywords

aromatic; Graphene; organic; Benzannulation; PAH; Polymer; Organic chemistry

Committee Chair

Dichtel, William R

Committee Member

Coates, Geoff
Ober, Christopher K

Degree Discipline

Chemistry and Chemical Biology

Degree Name

Ph. D., Chemistry and Chemical Biology

Degree Level

Doctor of Philosophy

Types

dissertation or thesis