Master's Theses

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Date of Award

Summer 1965

Degree Name

Master of Science (MS)




James H. MeMechan


The Claisen-Schmidt condensation has been evaluated for the synthesis of 21-hydroxychalcones. Previous methods, utilizing this condensation for synthesis, have been found to have any undesirable features. To eliminate these features and thus to extend the applicability of the condensation, a new reaction medium, dimethyl sulfoxide, has been employed. The use of dimethyl sulfoxide has given rise to a superior synthetic procedure. The most valuable features of this procedure are the reduced reaction time, increased yield of the chalcone, and a relatively pure, easily manipulated reaction product. In the course of this study two closely related areas have been investigated. The Baker-Venkataraman rearrangement, a specialized case of the Claisen-Schmidt condensation, has been found to progress well in dimethyl sulfoxide. The isomerization characteristics of 2-hydroxychalcones have been determined.


Copyright 1965 Edward Hong


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