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Thesis (M.S.)—University of Nebraska—Lincoln, 1933. Department of Chemistry.


Copyright 1933, the author. Used by permission.


4-Methyl-ω-Benzalacetophenone may be condensed with various esters and the nitrile of phenyl acetic acid resulting in products which may be converted into acids showing close relationship to a series of α-β- δ-ketonic acids of the following structure:




Work with these acids is comparatively recent and has been worked out carefully by Avery and his collaborators. From an inspection of the type formula it is apparent that a large number of such acids are possible by varying the R radical attached to the ketone group. Since two asymmetric carbons are present it should be possible to synthesize two optically inactive stereoisomers.

As this paper deals with ring substitution in these δ-ketonic acids a review of previous work, involving similar substitution will be given. Practically all of the compounds of this group studied in the past have had for the R group, a phenyl radical or a substituted phenyl group.

It was anticipated at the outset of this investigation that a study of isomeric relations would be made upon a series of compounds analogous to the benzoyl series prepared by Avery and Hall and mentioned in the introduction. But so many negative results were obtained it was thought advisable to study the effect of the methyl group in the synthesis of certain δ-ketonic acids. It was not the purpose of this investigation, however, to merely prepare a large number of δ-ketonic acids containing different R groups, but rather to study one or more series of compounds in comparison with the δ-ketonic acids and their derivatives prepared previously in this laboratory.

Advisor: Samuel Avery