Author

Heise

Date of Award

12-1985

Degree Name

Master of Arts

Department

Chemistry

First Advisor

Dr. Robert E. Harmon

Second Advisor

Dr. Dean W. Cooke

Third Advisor

Dr. Donald C. Berndt

Access Setting

Masters Thesis-Open Access

Abstract

Experiment 1: The reaction of various glutaconaldehyde salts (Na+ or K+) with glycosyl isothiocyanates has resulted in the formation of a novel class of compounds. Relatively mild conditions were utilized for the synthesis which occurs in four steps, and in good yield, starting from glucpseptentaacetate. These reactions were found to be regiospecific. The unique physical and spectral properties of the model compound 1-(2,3,4,6-tetra-0-acetyl-β-D-glycopranosyl)-2-thiono-3-pyridine carboxaldehyde are also discussed.

Experiement 2: Early synthetic methodologies have recently been utilized in the synthesis of 4-aryl-2-oxytetronimides. These compounds have been found to participate in condensation reactions with various substituted o-phenylene diamines. A study of oxidation techniques was also conducted which yielded 4-aryl-2, 3-dioxabutyro-1,4-lactones. The physical and spectral properties of these compounds are also discussed.

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