Reynolds, Rosalie D.
M.S. (Master of Science)
Department of Chemistry
Besides the reactions which are typical of dialdehydes, ?-phthalaldehyde undergoes many atypical reactions. The purpose of this research was to Investigate the base-catalyzed condensations of ?-phthalaldehyde with a number of alkyl amides (fomamide, proplonamlde, n-butyram1de, methyl urea, methoxyacetamlde and trimethyl acetamide) and aryl amides (benzamlde, ?-methoxybenzam1de, and ?-chlorobenzamlde). 1,3-D1hydroxyl solndollne derivatives were obtained from the condensation reactions Involving the straight chain alkyl amides. Trimethylacetamide, when condensed under the same conditions, gave the 1-hydroxy-phthalane derivative. When aryl amides were condensed under similar conditions, 1-hydroxy- or 1-ethoxyphthalane derivatives were obtained, depending upon the system being Investigated. Chemical and physical methods were used in support of the structures of these derivatives. The proposed mechanisms are presented along with the theoretical explanation of formation of the assigned structures. In the base-catalyzed condensation reaction of o-phthalaldehyde and acetanilide, no products were obtained.
Arendsen, David L., "Some base-catalyzed reactions of ?-phthalaldehyde with alkyl and aryl amides" (1968). Graduate Research Theses & Dissertations. 4976.
ix, 69 pages
Northern Illinois University
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