Date of Award


Degree Name

Master of Arts



First Advisor

Dr. George B. Trimitsis

Second Advisor

Dr. Don C. Iffland

Third Advisor

Dr. Dean W. Cooke

Access Setting

Masters Thesis-Open Access


I. Introduction

It is well known that the hydrogen atoms of a methyl group directly attached to an aromatic system are sufficiently acidic to be abstracted by suitable bases to generate the corresponding α-anion.1,2 These monoanions have frequently served as suitable intermediates for the formation of a large variety of a-condensation products in good to excellent yields2 On the other hand, attempts to obtain α,α-dianions from various dimethylaromatic systems have met with limited success.2 Due to the lack of sufficiently strong bases, dimetalation products were obtained only in poor yields even at high temperatures and prolonged reaction times, and their use in synthetic transformations has been very limited.

The purpose of the present investigation was to develop new and efficient methods capable of transforming dimethylarenes into their α,α-dianions under mild conditions and short reaction times, and to investigate the suitability of such dianions in various synthetic transformations.

More specifically, the present study sought to develop a new basic system capable of transforming 1,3-dimethylnapthalene into its α,α-dianion and to examine the reactions of this dianion with a variety of electrophilic reagents such as alkyl halides, ketones, and carbon dioxide.

1,3-Dimethylnapthalene was specficially chosen for this study because of its relative ease of preparation, and because of the expectation that its behavior would be representative of a large variety of other mononuclear and polynuclear aromatic hydrocarbons.

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