Date of Award
Bachelor of Science
The purpose of this project was to synthesize acenaphth (1, 2-a) acenaphth (1, 2-a) acenaphthene. The project originally followed Letsinger's preparation of a synthetic precursor called acenaphth (1, 2-a) acenaphthylene, which was to be dibrominated, giving the cis-6b, 12b derivative. This derivative was to be reacted with naphthalene to yield the desired product; but this route was abandoned when a necessary forerunner of Letsinger's hydrocarbon called 1, 8-dibromonaphthalene was obtained in very low yield. An alternate procedure leading to Letsinger's hydrocarbon, involving the Friedel-Crafts addition of 1, 8-di (chloromethyl) - naphthalene to naphthalene, was devised, and a synthetic precursor of the former compound called 1, 8-dimethylolnaphthalene was obtained. Three shorter Friedel-Crafts and related closures were attempted. First, acenaphthene was stirred with naphthalene in the presence of a catalytic amount of palladium-on-carbon. Second, acenaphthylene was stirred with naphthalene in cyclehexane in the presence of excess aluminum chloride. Third, the previous reaction was repeated with acenaphthylene which had been dibrominated. Gas chromatography showed no products were formed in the first two reactions, while the results for the third reaction were not definitive.
Gerson, John Isaac, "Toward a synthesis of acenaphth (1,2-a) acenaphth (1,2-a) acenaphthene" (1969). Honors Theses. 1795.