2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of salicylaldehyde (12.21 g/10.62 mL) in 70° C. ethanol (100 mL) was added ethylenediamine (3.01 g/3.33 mL). A yellow crystalline material immediately formed, and the reaction mixture was allowed to cool to room temperature with stirring. The solution was filtered, and the crystals were washed with cold ethanol. The ethanol layers were ombined and reduced to approximately 20 mL and allowed to stand at 0° C. overnight. The resulting crystals were collected by vacuum filtration and washed with water. The collected solids were dried in vacuo to obtain 13.15 g (98%) N,N′-bis(salicylidene)ethylenediamine as yellow platelets with a melting point of 126° C. (literature value (24) 127-128° c.). 1H NMR (DMSO-d6) δ 8.57 (s 2H, HC=N), 7.42 (d, 2H aromatic, J=7.3 Hz), 7.31 (t, 2H, aromatic, J=9.0 Hz), 6.88 (t, 4H, aromatic, J=8.3, 16.1 Hz), 3.89 (s, 4H, CH2). 13C NMR (DMSO-d6) δ 166.94 (2C, CO−), 160.57 (2C, HC+N), 132.38 (2C, aromatic), 131.69 (4C, aromatic), 118.59 (2C, aromatic), 116.51 (2C, aromatic), 58.88 (2C, CH2). A yellow crystalline material immediately formed The solution was filtered the crystals were washed with cold ethanol The resulting crystals were collected by vacuum filtration washed with water The collected solids were dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 1 mmol of SALEN ligand dissolved in acetic acid solution was loaded into each reactor tube of the Multiclave™, and 5 ml of 4:1 (weight ratio) water/EO was added at 100° C. The results are shown in Table 3. was added at 100° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 0.6 g of SALEN ligand dissolved in 1 ml water was loaded into each reactor tube of the Multiclave™, and 5 ml of 4:1 (weight ratio) water/EO was added at 100° C. The reactor was blanketed with 250 psig of N2. The experiment with the same SALEN ligand dissolved in 5 ml of water and treated with carbon dioxide over the weekend at room temperature was repeated but with 250 psig of CO2 as blanket gas. was added at 100° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 0.6 g of SALEN ligand dissolved in 1 ml water was loaded into each reactor tube of the Multiclave™, and 5 ml of 4:1 (weight ratio) water/EO was added at 100° C. The reactor was blanketed with 250 psig of N2. The experiment with the same SALEN ligand dissolved in 5 ml of water and treated with carbon dioxide over the weekend at room temperature was repeated but with 250 psig of CO2 as blanket gas. was added at 100° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of salicylaldehyde (12.21 g/10.62 mL) in 70° C. ethanol (100 mL) was added ethylenediamine (3.01 g/3.33 mL). A yellow crystalline material immediately formed, and the reaction mixture was allowed to cool to room temperature with stirring. The solution was filtered, and the crystals were washed with cold ethanol. The ethanol layers were combined and reduced to approximately 20 mL and allowed to stand at 0° C. overnight. The resulting crystals were collected by vacuum filtration and washed with water. The collected solids were dried in vacuo to obtain 13.15 g (98%) N,N′-bis(salicylidene)ethylenediamine as yellow platelets with a melting point of 126° C. (literature value (24) 127-128° C.). 1H NMR (DMSO-d6) δ8.57 (s 2H, HC═N), 7.42 (d, 2H aromatic, J=7.3 Hz), 7.31 (t, 2H, aromatic, J=9.0 Hz), 6.88 (t, 4H, aromatic, J=8.3, 16.1 Hz), 3.89 (s, 4H, CH2). 13C NMR (DMSO-d6) δ166.94 (2C, CO), 160.57 (2C, HC+N), 132.38 (2C, aromatic), 131.69 (4C, aromatic), 118.59 (2C, aromatic), 116.51 (2C, aromatic), 58.88 (2C, CH2). A yellow crystalline material immediately formed The solution was filtered the crystals were washed with cold ethanol The resulting crystals were collected by vacuum filtration washed with water The collected solids were dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Ethylenediamine (5.71 g, 0.095 mmol) was dissolved into toluene (60 ml). To it, a catalytic amount of acetic acid was added. Then, salicylaldehyde (23.20 g, 0.190 mmol) dissolved into toluene (60 ml) was dropwise added into the above solution. The resulting solution was then stirred at room temperature overnight. A yellowish crystalline product was precipitated. It was filtered, washed with ethanol, and dried. The yield was 23.7 g (93%). 1H NMR (300 MHz, CDCl3): δ=3.84 ppm (s, 4H), 6.85 ppm (t, 2H), 6.92 ppm (d, 2H), 7.17 ppm (m. 2H), 7.19 ppm (m, 2H), 8.28 ppm (s, 2H), 12.77 (s, broad, 2×OH); ESI MS: calcd. for C16H16N2O2, 268.3, found 269.2 (M+1); UV/Vis (λmax, nm, in methanol): 212, 255, 316, 400; IR (cm−1, nujol mull): 1610 (m, —C═N—). was dropwise added into the above solution A yellowish crystalline product was precipitated It was filtered washed with ethanol dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of salicylaldehyde (12.21 g/10.62 mL) in 70° C. ethanol (100 mL) was added ethylenediamine (3.01 g/3.33 mL). A yellow crystalline material immediately formed, and the reaction mixture was allowed to cool to room temperature with stirring. The solution was filtered, and the crystals were washed with cold ethanol. The ethanol layers were ombined and reduced to approximately 20 mL and allowed to stand at 0° C. overnight. The resulting crystals were collected by vacuum filtration and washed with water. The collected solids were dried in vacuo to obtain 13.15 g (98%) N,N′-bis(salicylidene)ethylenediamine as yellow platelets with a melting point of 126° C. (literature value (24) 127-128° C.). 1H NMR (DMSO-d6) δ 8.57 (s 2H, HC═N), 7.42 (d, 2H aromatic, J=7.3 Hz), 7.31 (t, 2H, aromatic, J=9.0 Hz), 6.88 (t, 4H, aromatic, J=8.3, 16.1 Hz), 3.89 (s, 4H, CH2). 13C NMR (DMSO-d6) δ 166.94 (2C, CO−), 160.57 (2C, HC+N), 132.38 (2C, aromatic), 131.69 (4C, aromatic), 118.59 (2C, aromatic), 116.51 (2C, aromatic), 58.88 (2C, CH2). A yellow crystalline material immediately formed The solution was filtered the crystals were washed with cold ethanol The resulting crystals were collected by vacuum filtration washed with water The collected solids were dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of salicylaldehyde (12.21 g/10.62 mL) in 70° C. ethanol (100 mL) was added ethylenediamine (3.01 g/3.33 mL). A yellow crystalline material immediately formed, and the reaction mixture was allowed to cool to room temperature with stirring. The solution was filtered, and the crystals were washed with cold ethanol. The ethanol layers were combined and reduced to approximately 20 mL and allowed to stand at 0° C. overnight. The resulting crystals were collected by vacuum filtration and washed with water. The collected solids were dried in vacuo to obtain 13.15 g (98%) N,N′-bis(salicylidene)ethylenediamine as yellow platelets with a melting point of 126° C. (literature value (24) 127-128° C.). 1H NMR (DMSO-d6) δ 8.57 (s 2H, HC=N), 7.42 (d, 2H aromatic, J=7.3 Hz), 7.31 (t, 2H, aromatic, J=9.0 Hz), 6.88 (t, 4H, aromatic, J=8.3, 16.1 Hz), 3.89 (s, 4H, CH2). 13C NMR (DMSO-d6) δ 166.94 (2C, CO−), 160.57 (2C, HC+N), 132.38 (2C, aromatic), 131.69 (4C, aromatic), 118.59 (2C, aromatic), 116.51 (2C, aromatic), 58.88 (2C, CH2). A yellow crystalline material immediately formed The solution was filtered the crystals were washed with cold ethanol The resulting crystals were collected by vacuum filtration washed with water The collected solids were dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 1 mmol of SALEN ligand dissolved in acetic acid solution was loaded into each reactor tube of the Multiclave™, and 5 ml of 4:1 (weight ratio) water/EO was added at 100° C. The results are shown in Table 3. was added at 100° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 0.6 g of SALEN ligand dissolved in 1 ml water was loaded into each reactor tube of the Multiclave™, and 5 ml of 4:1 (weight ratio) water/EO was added at 100° C. The reactor was blanketed with 250 psig of N2. The experiment with the same SALEN ligand dissolved in 5 ml of water and treated with carbon dioxide over the weekend at room temperature was repeated but with 250 psig of CO2 as blanket gas. was added at 100° C

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of salicylaldehyde (12.21 g/10.62 mL) in 70° C. ethanol (100 mL) was added ethylenediamine (3.01 g/3.33 mL). A yellow crystalline material immediately formed, and the reaction mixture was allowed to cool to room temperature with stirring. The solution was filtered, and the crystals were washed with cold ethanol. The ethanol layers were ombined and reduced to approximately 20 mL and allowed to stand at 0° C. overnight. The resulting crystals were collected by vacuum filtration and washed with water. The collected solids were dried in vacuo to obtain 13.15 g (98%) N,N′-bis(salicylidene)ethylenediamine as yellow platelets with a melting point of 126° C. (literature value (24) 127-128° c.). 1H NMR (DMSO-d6) δ 8.57 (s 2H, HC=N), 7.42 (d, 2H aromatic, J=7.3 Hz), 7.31 (t, 2H, aromatic, J=9.0 Hz), 6.88 (t, 4H, aromatic, J=8.3, 16.1 Hz), 3.89 (s, 4H, CH2). 13C NMR (DMSO-d6) δ 166.94 (2C, CO−), 160.57 (2C, HC+N), 132.38 (2C, aromatic), 131.69 (4C, aromatic), 118.59 (2C, aromatic), 116.51 (2C, aromatic), 58.88 (2C, CH2). A yellow crystalline material immediately formed The solution was filtered the crystals were washed with cold ethanol The resulting crystals were collected by vacuum filtration washed with water The collected solids were dried in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Approximately 1 mmol of SALEN ligand dissolved in acetic acid solution was loaded into each reactor tube of the Multiclave™, and 5 ml of 4:1 (weight ratio) water/EO was added at 100° C. The results are shown in Table 3. was added at 100° C