0.1 M amine (0.5 mmol) and 0.4 M methyl formate (123 µL, 2.0 mmol) in toluene, solution B contained 0.01 M 127 (7 mg, 0.05 mmol) in toluene. Both solutions were injected into 5 mL sample loops then pumped through the reactor. The solutions combined at a T-piece and passed through the 10 mL flow reactor heated to 80 oC at a combined flow rate of 0.5 mL/min, resulting in a residence time of 20 minutes. The output stream of the reactor was collected and solvent removed under vacuum. Purification by column chromatography yielded the titled N-formamide. flow preparation of N-formamides using methyl formate and solution-phase 127 in methanol (method D) The Vapourtec R-series system was fitted with a 10 mL reactor, a 100 psi back-pressure regulator and primed with methanol. Two 2 mL solutions were prepared: solution A contained 1 M amine (2 mmol) and 4 M methyl formate (0.5 mL, 8 mmol) in methanol, solution B contained 0.1 M 127 (28 mg, 0.2 mmol) in methanol. Both solutions were injected into 2 mL sample loops then pumped through the reactor. The solutions combined at a and passed through the 10 mL flow reactor heated to 110 oC at a combined flow rate of 0.5 mL/min, resulting in a residence time of 20 minutes. The output stream of the reactor was collected and solvent removed under vacuum. Purification by column chromatography yielded the titled N-formamide. flow preparation of N-formamides methyl formate and phase 127 in methanol (method E) The Vapourtec R-series system was fitted with a portex column containing 1 gram of polystyrene-supported 127 (3 mmol/gram catalyst loading), a 100 psi back-pressure
0.1 M amine (0.5 mmol) and 0.4 M methyl formate (123 µL, 2.0 mmol) in toluene, solution B contained 0.01 M 127 (7 mg, 0.05 mmol) in toluene. Both solutions were injected into 5 mL sample loops then pumped through the reactor. The solutions combined at a T-piece and passed through the 10 mL flow reactor heated to 80 oC at a combined flow rate of 0.5 mL/min, resulting in a residence time of 20 minutes. The output stream of the reactor was collected and solvent removed under vacuum. Purification by column chromatography yielded the titled N-formamide. flow preparation of N-formamides using methyl formate and solution-phase 127 in methanol (method D) The Vapourtec R-series system was fitted with a 10 mL reactor, a 100 psi back-pressure regulator and primed with methanol. Two 2 mL solutions were prepared: solution A contained 1 M amine (2 mmol) and 4 M methyl formate (0.5 mL, 8 mmol) in methanol, solution B contained 0.1 M 127 (28 mg, 0.2 mmol) in methanol. Both solutions were injected into 2 mL sample loops then pumped through the reactor. The solutions combined at a and passed through the 10 mL flow reactor heated to 110 oC at a combined flow rate of 0.5 mL/min, resulting in a residence time of 20 minutes. The output stream of the reactor was collected and solvent removed under vacuum. Purification by column chromatography yielded the titled N-formamide. flow preparation of N-formamides methyl formate and 127 in methanol (method E) The Vapourtec R-series system was fitted with a portex column containing 1 gram of polystyrene-supported 127 (3 mmol/gram catalyst loading), a 100 psi back-pressure phase
Complete_thesis_with_corrections.docx