2-苯基丁-3-烯腈

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Vinyl benzylcyanide (2.2 g, 0.0154 mol) was dissolved in methanol (10 mL) and 4-(diphenylamino)benzaldehyde (1 ME, 0.0154 mol, 4.2 g) was added, followed by the addition of pyrrolidine (1.5 ME, 0.0231 mol, 1.64 g, 1.9 mL). The resulting reaction mixture was heated at reflux overnight under argon. TLC analysis on the mixture (H:EA, 8.5:1.5) showed the formation of a yellow coloured product along with some unreacted vinyl benzylcyanide. The reaction mixture was purified by column chromatography (hexane:ethyl acetate, 8.5:1.5). After chromatography, the pure product, AG1-78, was obtained as a yellow colloured brightly fluorescent material solid (1.5 g, 23%), 1H NMR (400 MHz, CDCl3) δ 5.3 (d, 1H, ethylene —CH), δ5.8 (d, 1H, ethylene-CH), δ 6.7 (m, 1H), δ 7.1 (m, 8H), δ 7.3 (m, 4H), δ 7.45 (m, 3H), δ 7.6 (dd, 2H), δ 7.7 (dd, 2H), 13C NMR (CDCl3, ppm, δ): 149.94, 146.60, 141.18, 137.85, 135.97, 134.34, 130.66, 129.56, 126.75, 126.44, 125.78, 125.70, 124.37, 120.89, 118.66, 114.81, 107.38. The resulting reaction mixture was heated at reflux overnight under argon The reaction mixture was purified by column chromatography (hexane:ethyl acetate, 8.5:1.5)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of vinylbenzyl chloride in acetonitrile (5.0 g, 0.033 mol, in 10 mL of ACN) was added to a mixture of potassium cyanide (1.5 ME, 0.0495 mol, 3.2 g), 18-Crown-6 ether (0.52 g) and acetonitrile (15 mL). The resulting mixture was stirred overnight at room temperature. TLC analysis (hexane:ethyl acetate, 8:2) indicated that the reaction had gone to completion. The reaction was worked up by adding water to the reaction mixture (50 mL) and extracting the product into ethyl acetate. The organic layer was washed twice with water followed by brine solution. The organic layer was dried on Na2SO4 and recovered under reduced pressure to obtain the required vinylbenzyl cyanide as a light brown coloured oil (4.2 g, 87.8%) which was used without further purification in the next step. 1H NMR (400 MHz, CDCl3) δ3.7 (s, 2H), δ 5.3 (d, 1H, ethylene —CH trans), δ5.8 (d, 1H, ethylene-CH cis), δ 6.7 (m, 1H), δ 7.3 (Ar 2H, dd), δ 7.4 (Ar 2H, dd). extracting the product into ethyl acetate The organic layer was washed twice with water The organic layer was dried on Na2SO4 recovered under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of vinylbenzyl chloride in acetonitrile (5.0 g, 0.033 mol, in 10 mL of ACN) was added to a mixture of potassium cyanide (1.5 ME, 0.0495 mol, 3.2 g), 18-Crown-6 ether (0.52 g) and acetonitrile (15 mL). The resulting mixture was stirred overnight at room temperature. TLC analysis (hexane:ethyl acetate, 8:2) indicated that the reaction had gone to completion. The reaction was worked up by adding water to the reaction mixture (50 mL) and extracting the product into ethyl acetate. The organic layer was washed twice with water followed by brine solution. The organic layer was dried on Na2SO4 and recovered under reduced pressure to obtain the required vinylbenzyl cyanide as a light brown coloured oil (4.2 g, 87.8%) which was used without further purification in the next step. 1H NMR (400 MHz, CDCl3) δ3.7 (s, 2H), δ 5.3 (d, 1H, ethylene —CH trans), δ5.8 (d, 1H, ethylene-CH cis), δ 6.7 (m, 1H), δ 7.3 (Ar 2H, dd), δ 7.4 (Ar 2H, dd). extracting the product into ethyl acetate The organic layer was washed twice with water The organic layer was dried on Na2SO4 recovered under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: a procedure according to A. Zerroukhi, A. Ainser, A. Arsac, N. Mignard, and B. Marculescu, Polymer Bulletin, 42, 535, 1999, is used. Initially, vinylbenzyl chloride is reacted with sodium cyanide to give vinylbenzyl cyanide, which is then reacted with ethanolamine to give the vinylbenzyloxazoline.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: a procedure according to A. Zerroukhi, A. Ainser, A. Arsac, N. Mignard, and B. Marculescu, Polymer Bulletin, 42, 535, 1999, is used. Initially, vinylbenzyl chloride is reacted with sodium cyanide to give vinylbenzyl cyanide, which is then reacted with ethanolamine to give the vinylbenzyloxazoline.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of vinylbenzyl chloride in acetonitrile (5.0 g, 0.033 mol, in 10 mL of ACN) was added to a mixture of potassium cyanide (1.5 ME, 0.0495 mol, 3.2 g), 18-Crown-6 ether (0.52 g) and acetonitrile (15 mL). The resulting mixture was stirred overnight at room temperature. TLC analysis (hexane:ethyl acetate, 8:2) indicated that the reaction had gone to completion. The reaction was worked up by adding water to the reaction mixture (50 mL) and extracting the product into ethyl acetate. The organic layer was washed twice with water followed by brine solution. The organic layer was dried on Na2SO4 and recovered under reduced pressure to obtain the required vinylbenzyl cyanide as a light brown coloured oil (4.2 g, 87.8%) which was used without further purification in the next step. 1H NMR (400 MHz, CDCl3) δ3.7 (s, 2H), δ 5.3 (d, 1H, ethylene —CH trans), δ5.8 (d, 1H, ethylene-CH cis), δ 6.7 (m, 1H), δ 7.3 (Ar 2H, dd), δ 7.4 (Ar 2H, dd). extracting the product into ethyl acetate The organic layer was washed twice with water The organic layer was dried on Na2SO4 recovered under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 12.2 g of commercially available vinylbenzyl chloride (a mixture of 60% of a meta-isomer and 40% of a para-isomer) were reacted with 5 g of NaCN in a mixed solvent of methanol/water=12.2 g/5 g at 64° C. for 12 hours. A reaction product solution was filtered, and the solvent was then distilled off, followed by distillation under reduced pressure, thereby obtaining 8.1 g of vinylbenzyl cyanide (yield 71%). A reaction product solution was filtered the solvent was then distilled off followed by distillation under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Vinyl benzylcyanide (2.2 g, 0.0154 mol) was dissolved in methanol (10 mL) and 4-(diphenylamino)benzaldehyde (1 ME, 0.0154 mol, 4.2 g) was added, followed by the addition of pyrrolidine (1.5 ME, 0.0231 mol, 1.64 g, 1.9 mL). The resulting reaction mixture was heated at reflux overnight under argon. TLC analysis on the mixture (H:EA, 8.5:1.5) showed the formation of a yellow coloured product along with some unreacted vinyl benzylcyanide. The reaction mixture was purified by column chromatography (hexane:ethyl acetate, 8.5:1.5). After chromatography, the pure product, AG1-78, was obtained as a yellow colloured brightly fluorescent material solid (1.5 g, 23%), 1H NMR (400 MHz, CDCl3) δ 5.3 (d, 1H, ethylene —CH), δ5.8 (d, 1H, ethylene-CH), δ 6.7 (m, 1H), δ 7.1 (m, 8H), δ 7.3 (m, 4H), δ 7.45 (m, 3H), δ 7.6 (dd, 2H), δ 7.7 (dd, 2H), 13C NMR (CDCl3, ppm, δ): 149.94, 146.60, 141.18, 137.85, 135.97, 134.34, 130.66, 129.56, 126.75, 126.44, 125.78, 125.70, 124.37, 120.89, 118.66, 114.81, 107.38. The resulting reaction mixture was heated at reflux overnight under argon The reaction mixture was purified by column chromatography (hexane:ethyl acetate, 8.5:1.5)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of vinylbenzyl chloride in acetonitrile (5.0 g, 0.033 mol, in 10 mL of ACN) was added to a mixture of potassium cyanide (1.5 ME, 0.0495 mol, 3.2 g), 18-Crown-6 ether (0.52 g) and acetonitrile (15 mL). The resulting mixture was stirred overnight at room temperature. TLC analysis (hexane:ethyl acetate, 8:2) indicated that the reaction had gone to completion. The reaction was worked up by adding water to the reaction mixture (50 mL) and extracting the product into ethyl acetate. The organic layer was washed twice with water followed by brine solution. The organic layer was dried on Na2SO4 and recovered under reduced pressure to obtain the required vinylbenzyl cyanide as a light brown coloured oil (4.2 g, 87.8%) which was used without further purification in the next step. 1H NMR (400 MHz, CDCl3) δ3.7 (s, 2H), δ 5.3 (d, 1H, ethylene —CH trans), δ5.8 (d, 1H, ethylene-CH cis), δ 6.7 (m, 1H), δ 7.3 (Ar 2H, dd), δ 7.4 (Ar 2H, dd). extracting the product into ethyl acetate The organic layer was washed twice with water The organic layer was dried on Na2SO4 recovered under reduced pressure

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: a procedure according to A. Zerroukhi, A. Ainser, A. Arsac, N. Mignard, and B. Marculescu, Polymer Bulletin, 42, 535, 1999, is used. Initially, vinylbenzyl chloride is reacted with sodium cyanide to give vinylbenzyl cyanide, which is then reacted with ethanolamine to give the vinylbenzyloxazoline.