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UBC Theses and Dissertations

The action of carbon monoxide and dicobalt octacarbonyl on some aromatic oximes O'Donnell, Joseph Patrick


When syn-benzaldoxime was reacted with carbon monoxide containing about 0.04 volume percent of hydrogen and dicobalt octacarbonyl in benzene solution at elevated temperatures and pressures the following compounds were produced; sym-dibenzylurea (35%), monobenzylurea (10%) and benzaldehyde (10%). Also isolated were 15% yields of two unidentified components referred to as compounds A and B. When benzophenone oxime was subjected to the same reaction conditions the major product was 3-phenylphthalimidine (75%). Also isolated was a 5% yield of an unidentified component called compound B. It was demonstrated that under the reaction conditions used considerable amounts of dicobalt octacarbonyl are needed for successful reaction. When the octacarbonyl was present in only catalytic amounts the course of the observed reaction was greatly affected and the major isolated product was benzophenone (70%). Small amounts of 3-phenylphthalimidine and of the original oxime were also isolated. When the 0-methyl ether of benzophenone oxime was reacted the only product isolated was 3-phenylphthalimidine in 75% yield. Reaction pressures corrected to constant temperature are plotted against reaction time for each substrate and the results discussed. A new method of synthesizing the 0-methyl ether of benzophenone oxime (using 0-methyl hydroxylamine), and a dichromate-acetic acid oxidation of sym-dibenzylurea giving a high yield of dibenzoylurea are described. A platinum oxide in acetic acid reduction of 3-phenylphthalimidine which reduced both benzene rings but left the lactam group intact is also described. Infrared spectra are included for all compounds obtained.

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