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Date of Award


Document Type


Degree Name

Master of Science (M.S.)


Graduate School

First Advisor

Charles A. Matuszak

First Committee Member

Paul H. Gross

Second Committee Member

Herschel G. Frye


The use of alkali and alkaline earth metals as reducing agents in liquid ammonia solvent for aromatic and conjugated systems has been investigated by chemists at least since the early 1900's, e.g., Lebau and Picon (1). By subsequent additions of a proton source, the system yielded the first successful partial reduction of a monobenzenoid system, as reported by Wooster and Godfrey (2), in 1937. As a result of that success a patent was issued to Wooster for the process (3). Little additional work was reported until Birch and his co-workers picked up the investigation in the early 1940's. It was through his vigorous study and development of this reduction system that Birch's name came to be associated with reductions of organic compounds by alkali metals in liquid ammonia, hence, the Birch reduction.

In this thesis the Birch reduction of cinnamic acid is investigated.