Publication Date


Document Type


First Advisor

Reynolds, Rosalie D.

Degree Name

M.S. (Master of Science)

Legacy Department

Department of Chemistry




No completely unsaturated mono-nitrogen heterocycles containing more than seven atoms in the ring have ever been synthesized. This work involved attempted synthesis of either [2,3]-benzazocine or [2,3,6,7]-dibenzazoclne, both of which contain a completely unsaturated mono-nitrogen eight-membered heterocycle. This was attempted by use of a base-catalyzed condensation of o-toluidine and either diethyl maleate or diethyl phthalate. The initial objective was not realized. However, the results that were obtained were not without significance. The base-catalyzed condensation of diethyl phthalate and o-toluidine resulted in the formation of the di-o-toluidide of phthalic acid. The di-p-toluidide and dianilide of phthalic acid also were prepared. The significance of the preparation of the di-o-toluidide and di-p-toluidide is that they are compounds that have not been previously reported. The dianilide of phthalic acid was very useful in the proof of structure of the ditoluidides, since the dianilide had previously been prepared by another method. The entire proof of structure is described in the thesis. The methods used in the structure proof utilized, among other techniques, n.m.r. and IR.-spectra, which were new and beneficial experiences to this Investigator. The significance of the research stems from the possibility that a new and general preparative method for diamides of diesters has been discovered. The reaction also may well be applicable to the formation of dinitrogen ring systems.


Includes bibliographical references.||Includes illustrations.


vi, 29 pages




Northern Illinois University

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