Oxime NMR Scan
This is the NMR scan of the oxime which is also the starting material of the cyclization reaction. An NMR scan produces a graph that can be analyzed to understand the structure and purity of compounds. The above NMR depicts a couplet of symmetric peaks at 6.9 and 7.6 ppm. These indicate the existence of the benzene ring in the left-hand side of the oxime. There is also a forest of peaks at 6.0 as well as 5.2. The one at 6.0 represents the double bond, which we want to disappear after the cyclization, and the one at 5.2 represents the hydrogen bonded to second carbon from the right. There are no distinguishing peaks from 2.5 to 3.4, where we would find isoxazoline. This means we have a clean starting material.
Palladium (II) Chloride NMR Scan
The above NMR scan is the 5% Palladium (II) Chloride cyclization with 300% Copper (II) Chloride. The couplet of symmetric peaks at 6.9 and 7.6 ppm are gone as well as the forests at 6.0 and 5.2 ppm. This scan also reveals cluttered, irregular peaks from 2.5 to 3.4 ppm. Due to the disappearance of the couplet of symmetric peaks, the benzene ring has disintegrated. Interestingly, both forests have disappeared, meaning the right side of the compound has fallen apart as well. The peaks from 2.5 to 3.4 show very weak signals, indicating only trace amounts of isoxazoline were successfully synthesized.
Nickel (II) Chloride NMR Scan
The above picture was of the Nickel (II) Chloride one equivalent cyclization. There was a couplet of symmetric peaks at 6.9 and 7.6 ppm as well as the forests of peaks at 5.2 and 6.9 ppm. There were faint symmetric signals at 2.7 ppm. The benzene ring is still intact due to the couplet of symmetric peaks at 6.9 and 7.6. However, most of the starting material remains as indicated by the existence of the forest at 6.0 because the isoxazoline doesn't have any double bonds. There were very small traces of isoxazoline that were produced as indicated by the signals at 2.7.
Lead (II) Acetate NMR Scan
The above picture was of the Lead (II) Acetate one equivalent cyclization. There was a couplet of symmetric peaks at 6.9 and 7.6 ppm as well as the forests of peaks at 5.2 and 6.9 ppm. There were faint symmetric signals at 2.7 ppm. The benzene ring is still intact due to the couplet of symmetric peaks at 6.9 and 7.6. However, most of the starting material remains as indicated by the existence of the forest at 6.0 because the isoxazoline doesn't have any double bonds. This cyclization produced the strongest signals in the 2.5 to 3.4 range compared to the other cyclizations, meaning that isoxazoline was produced in higher concentrations here than the other cyclizations.