Date of Award
Doctor of Philosophy
Dr. Robert E. Harmon
This report describes the synthesis of naphthalene-2,3-dialdehyde, and an analytical method for determining its purity by thin layer chromatography. Subsequently, the dialdehyde was condensed with various cyclic ketones to generate a series of polymethylene bridged naphthotropones. It was found that planarity and aromaticity increase with the size of the methylene bridge, although, the bridge must contain six or more methylene groups for the latter to be true. The claim for aromaticity is supported by NMR and IR data, which indicates the positive charge for a perchlorate cation salt is delocalized over the naphthalene and tropone ring system. Furthermore, from the available data, the order of aromaticity for the following tropone derivatives is: tropone > naphthotropone > benzotropone > pyraxolotropone > furotropone.
Crapps, Edward O., "Naphthalene-2,3-Dialdehyde: A Synthon to 7,9-Polymethylene-8H-Cyclohepta[B]Naphthalene-8-One and a Study of Their Aromaticity" (1984). Dissertations. 2380.