1,1,2,3,3-pentamethylguanidine

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Allyl acetate (21.6 μL, 200 μmol) was added to a solution of triethylamine (56 μL, 400 μmol) or pentamethylguanidine (51.7 mg, 400 μmol) and 4-benzyl-2-phenyl-2-oxazolin-5-one (450 μmol) in acetonitrile (1 mL). Then a preformed solution of bis(η3 -allyl)di-,μ-chlorodipalladium (II) (1.8 mg, 4.9 μmol) and ligand 1 (10.4 mg, 15.1 μmol) in acetonitrile (1 mL) was added via cannula. The reaction mixture was quenched with aqueous phosphate buffer (pH 7, 40 ml) and extracted with CH2Cl2 (3×30 mL). The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with petroleum ether-AcOEt (95:5) to give 4-allyl-4-benzyl-2-phenyl-2-oxazolin-5-one. ##STR15## The reaction mixture was quenched with aqueous phosphate buffer (pH 7, 40 ml) extracted with CH2Cl2 (3×30 mL) The combined organic layer was dried over Na2SO4 concentrated in vacuo The residue was purified by flash chromatography on silica gel eluting with petroleum ether-AcOEt (95:5)

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A perfluorinated polymer precursor (film thickness: 25 μm, sulfonyl fluoride form, EW1100) was treated with 1,1,3,3-tetramethylguanidine in dimethylformamide (DMF) solution at 90° C. for 24 hr. After washing with water, the membrane was dried under a vacuum plate at 75° C. The absorption by C═N was observed at 1525-1580 cm−1 by FT-IR, and C═N and N—CH3 peak was observed at 162 and 39.5 ppm by C-NMR, respectively. Tetramethlguanidine functionalized perfluorinated polymers were further treated with dimethyl sulfate (DMS) in DMF at 90° C. for 24 hr. Pentamethylguanidine functionalized perfluorinated polymer was obtained. Guanidine functionalized perfluorinated polymers were further treated with 1 M NaOH for 4 hr at boiling temperature followed by washing with water. After washing with water the membrane was dried under a vacuum plate at 75° C The absorption by C═N Tetramethlguanidine functionalized perfluorinated polymers were further treated with dimethyl sulfate (DMS) in DMF at 90° C. for 24 hr

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

Procedure: Tetramethlguanidine functionalized perfluorinated polymers were further treated with dimethyl sulfate (DMS) in DMF at 90° C. for 24 hr. Pentamethylguanidine functionalized perfluorinated polymer was obtained. Guanidine functionalized perfluorinated polymers was further treated with 1 M NaOH followed by washing with water.

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

Procedure: Tetramethlguanidine functionalized perfluorinated polymers were further treated with dimethyl sulfate (DMS) in DMF at 90° C. for 24 hr. Pentamethylguanidine functionalized perfluorinated polymer was obtained. Guanidine functionalized perfluorinated polymers was further treated with 1 M NaOH followed by washing with water.

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

Procedure: Tetramethlguanidine functionalized perfluorinated polymers were further treated with dimethyl sulfate (DMS) in DMF at 90° C. for 24 hr. Pentamethylguanidine functionalized perfluorinated polymer was obtained. Guanidine functionalized perfluorinated polymers was further treated with 1 M NaOH followed by washing with water.

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

Procedure: Allyl acetate (21.6 μL, 200 μmol) was added to a solution of triethylamine (56 μL, 400 μmol) or pentamethylguanidine (51.7 mg, 400 μmol) and 4-benzyl-2-phenyl-2-oxazolin-5-one (450 μmol) in acetonitrile (1 mL). Then a preformed solution of bis(η3 -allyl)di-,μ-chlorodipalladium (II) (1.8 mg, 4.9 μmol) and ligand 1 (10.4 mg, 15.1 μmol) in acetonitrile (1 mL) was added via cannula. The reaction mixture was quenched with aqueous phosphate buffer (pH 7, 40 ml) and extracted with CH2Cl2 (3×30 mL). The combined organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with petroleum ether-AcOEt (95:5) to give 4-allyl-4-benzyl-2-phenyl-2-oxazolin-5-one. ##STR15## The reaction mixture was quenched with aqueous phosphate buffer (pH 7, 40 ml) extracted with CH2Cl2 (3×30 mL) The combined organic layer was dried over Na2SO4 concentrated in vacuo The residue was purified by flash chromatography on silica gel eluting with petroleum ether-AcOEt (95:5)

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

Procedure: A perfluorinated polymer precursor (film thickness: 25 μm, sulfonyl fluoride form, EW1100) was treated with 1,1,3,3-tetramethylguanidine in dimethylformamide (DMF) solution at 90° C. for 24 hr. After washing with water, the membrane was dried under a vacuum plate at 75° C. The absorption by C═N was observed at 1525-1580 cm−1 by FT-IR, and C═N and N—CH3 peak was observed at 162 and 39.5 ppm by C-NMR, respectively. Tetramethlguanidine functionalized perfluorinated polymers were further treated with dimethyl sulfate (DMS) in DMF at 90° C. for 24 hr. Pentamethylguanidine functionalized perfluorinated polymer was obtained. Guanidine functionalized perfluorinated polymers were further treated with 1 M NaOH for 4 hr at boiling temperature followed by washing with water. After washing with water the membrane was dried under a vacuum plate at 75° C The absorption by C═N Tetramethlguanidine functionalized perfluorinated polymers were further treated with dimethyl sulfate (DMS) in DMF at 90° C. for 24 hr

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

Procedure: A perfluorinated polymer precursor (film thickness: 25 μm, sulfonyl fluoride form, EW1100) was treated with 1,1,3,3-tetramethylguanidine in dimethylformamide (DMF) solution at 90° C. for 24 hr. After washing with water, the membrane was dried under a vacuum plate at 75° C. The absorption by C═N was observed at 1525-1580 cm−1 by FT-IR, and C═N and N—CH3 peak was observed at 162 and 39.5 ppm by C-NMR, respectively. Tetramethlguanidine functionalized perfluorinated polymers were further treated with dimethyl sulfate (DMS) in DMF at 90° C. for 24 hr. Pentamethylguanidine functionalized perfluorinated polymer was obtained. Guanidine functionalized perfluorinated polymers were further treated with 1 M NaOH for 4 hr at boiling temperature followed by washing with water. After washing with water the membrane was dried under a vacuum plate at 75° C The absorption by C═N Tetramethlguanidine functionalized perfluorinated polymers were further treated with dimethyl sulfate (DMS) in DMF at 90° C. for 24 hr

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

Procedure: To a mixture of 0.1 mol of bis(2-cyanoethyl)phosphine oxide and 0.1 mol of acetone was added 1.0 gram of either triethyl amine or pentamethyl guanidine. The mixture was heated for 2 hours at steam bath temperatures. The resulting solid was filtered and recrystallized from acetone to give an 88% yield of product, m.p. 124°-125° C. The mixture was heated for 2 hours at steam bath temperatures The resulting solid was filtered recrystallized from acetone

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

Procedure: Tetramethlguanidine functionalized perfluorinated polymers were further treated with dimethyl sulfate (DMS) in DMF at 90° C. for 24 hr. Pentamethylguanidine functionalized perfluorinated polymer was obtained. Guanidine functionalized perfluorinated polymers was further treated with 1 M NaOH followed by washing with water.