di(propan-2-yl)phosphane

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.46 g (10 mmol) of 1,3-bis(hydroxymethyl)ferrocene and 4.72 g (40 mmol) of diisopropylphosphine were added to 40 ml of acetic acid. The resulting mixture was heated at 80° C. for 3.5 hours and extracted with benzene after cooling. The organic phase was then washed with water and then dried over Na2SO4. After evaporation an orange residue was chromatographed on an alumina column. Elution with an ether-light petroleum mixture yielded 3.92 g (88%) of the product. Selected NMR data (CDCl3, 22° C.) 1H: δ0.92 (m, 24H, CH3), 1.63 (m, 4H, CH(CH3)2), 2.49 (bs, 4H, CH2P), 3.92 (s, 5H, C5H5), 3.95 (bs, 2H, 4.5-H), 4.06 (bs, 1H, 2-H). 31P NMR (CDCl3, 22° C.): δ 10.97(s, 2P). extracted with benzene after cooling The organic phase was then washed with water dried over Na2SO4 After evaporation an orange residue was chromatographed on an alumina column Elution with an ether-light petroleum mixture

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.46 g (10 mmol) of 1,3-bis(hydroxymethyl)ferrocene and 4.72 g (40 mmol) of diisopropylphosphine were added to 40 ml of acetic acid. The resulting mixture was heated at 80° C. for 3.5 hours and extracted with benzene after cooling. The organic phase was then washed with water and then dried over Na2SO4. After evaporation an orange residue was chromatographed on an alumina column. Elution with an ether-light petroleum mixture yielded 3.92 g (88%) of the product. Selected NMR data (CDCl3, 22° C.) 1H: δ0.92 (m, 24H, CH3), 1.63 (m, 4H, CH(CH3)2), 2.49 (bs, 4H, CH2P), 3.92 (s, 5H, C5H5), 3.95 (bs, 2H, 4.5-H), 4.06 (bs, 1H, 2-H). 31P NMR (CDCl3, 22° C.): δ 10.97(s, 2P). extracted with benzene after cooling The organic phase was then washed with water dried over Na2SO4 After evaporation an orange residue was chromatographed on an alumina column Elution with an ether-light petroleum mixture

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

Procedure: The title compound was prepared in accordance with the procedure of Example 10 employing di-iso-propylphosphine (Digital Speciality Chemicals 392 mg, 3.33 mmol), 1,2-bis(dimethylaminomethyl)ferrocene (0.5 g, 1.66 mmol) and anhydrous acetic acid (100 ml). Yield 0.262 g.

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

Procedure: The title compound was prepared in accordance with the procedure of Example 10 employing di-iso-propylphosphine (Digital Speciality Chemicals 392 mg, 3.33 mmol), 1,2-bis(dimethylaminomethyl)ferrocene (0.5 g, 1.66 mmol) and anhydrous acetic acid (100 ml). Yield 0.262 g.

Conditions: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: stirring bar was added 6-chloromethyl-2,2′-bipyridine (BPy-CH2Cl) (1.03 g, 5.00 mmol), di-iso-propyl phosphine (710 mg, 6.00 mmol), and 15 mL MeOH in nitrogen glove box. The flask was sealed and heated at 50° C. for 48 hrs with stirring outside the glove box. After cooling, it was reintroduced to the glove box, triethylamine (910 mg, 9.00 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr. The solvents were removed under reduced pressure to obtain a white solid. The residue was washed with ether (2×10 mL), filtered and was removed under reduced pressure to yield a pale yellow liquid. It was further purified by basic alumina chromatography under the glove box using hexane as an eluent to yield pure 6. The flask was sealed with stirring outside the glove box After cooling was added the reaction mixture was stirred at room temperature for 1 hr The solvents were removed under reduced pressure to obtain a white solid The residue was washed with ether (2×10 mL) filtered was removed under reduced pressure to yield a pale yellow liquid It was further purified by basic alumina chromatography under the glove box to yield pure 6

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

Procedure: The title compound was prepared in accordance with the procedure of Example 2 employing di-iso-propylphosphine (Digital Speciality Chemicals 392 mg, 3.33 mmol), 1,2-bis(dimethylaminomethyl)ferrocene (0.5 g, 1.66 mmol) and anhydrous acetic acid (100 ml). Yield 0.262 g.

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

Procedure: Following the procedure described for the synthesis of 3 (method A), 15.81 g (0.081 mol) of 2-bromo-1H-indene, 9.54 g (0.081 mol) of iPr2PH, 13.9 ml (10.09 g, 0.100 mol) of Et3N, and 2.95 g (2.55 mmol) of Pd(PPh3)4 in 60 ml of toluene gave 1H-Inden-2-yl(diisopropyl)phosphine. The crude product was distilled in vacuum (104–106° C./2 mm). Yield 14.8 g (80%) of colorless oil of 1H-Inden-2-yl(diisopropyl)phosphine, 4.

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2.46 g (10 mmol) of 1,3-bis(hydroxymethyl)ferrocene and 4.72 g (40 mmol) of diisopropylphosphine were added to 40 ml of acetic acid. The resulting mixture was heated at 80° C. for 3.5 hours and extracted with benzene after cooling. The organic phase was then washed with water and then dried over Na2SO4. After evaporation an orange residue was chromatographed on an alumina column. Elution with an ether-light petroleum mixture yielded 3.92 g (88%) of the product. Selected NMR data (CDCl3, 22° C.) 1H: δ0.92 (m, 24H, CH3), 1.63 (m, 4H, CH(CH3)2), 2.49 (bs, 4H, CH2P), 3.92 (s, 5H, C5H5), 3.95 (bs, 2H, 4.5-H), 4.06 (bs, 1H, 2-H). 31P NMR (CDCl3, 22° C.): δ 10.97(s, 2P). extracted with benzene after cooling The organic phase was then washed with water dried over Na2SO4 After evaporation an orange residue was chromatographed on an alumina column Elution with an ether-light petroleum mixture

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

Procedure: The title compound was prepared in accordance with the procedure of Example 10 employing di-iso-propylphosphine (Digital Speciality Chemicals 392 mg, 3.33 mmol), 1,2-bis(dimethylaminomethyl)ferrocene (0.5 g, 1.66 mmol) and anhydrous acetic acid (100 ml). Yield 0.262 g.