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UBC Theses and Dissertations

The action of carbon monoxide and hydrogen on deoxybenzoin oxime and on 2-acetonaphthone oxime Hubscher, Arthur Ronald


When deoxybenzoin oxime was reacted with carbon monoxide and hydrogen in the presence of dicobalt ootacarbonyl at elevated temperatures and pressures 3-benzylphthalimidine and 3-phenyl-3,4-dihydroisocarbostyryl were produced. When 2-acetonaphthone oxime was reacted under similar conditions 2-(β-naphthyl)-4-methyl-benzo[h] quinoline, 3-methylbenzo[f]phthalimidine and 1- (β-naphthyl)ethylurea were produced. Verification of the structure of 2-(β-naphthyl)-4-methylbenzo[h]-quinoline was attained in part through the hydrochloride salt, the methiodide salt, the picrate derivative and the 2-(β-naphthyl)-4-formylbenzof[h]-quinoline derivative. 2-(β-Naphthyl)-4-methyl-benzof[h] quinoline was also synthesized by reacting 2- acetonaphthone oxime with 2-acetonaphthone at elevated temperatures. The infrared spectra of the above compounds are described.

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