3-chloropropyl(diphenyl)phosphane

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL round bottom flask there was added 400 mL of dry tetrahydrofuran followed by 0.081 mole of HPPh2. The mixture was cooled to 0° C. and 0.081 mole of n-butyl lithium was slowly added to generate LiPPh2 ; this was slowly warmed to room temperature and stirred for about one hour. The solution was transferred to a dropping funnel and added dropwise to a flask containing 100 mL of 1,3-dichloropropane dissolved in 100 mL of diethyl ether. After stirring overnight the mixture was hydrolyzed with 25 mL of water. The organic layer was separated and the solvent removed by vacuum to leave Ph2P(CH2)3Cl that was stored under nitrogen until needed. this was slowly warmed to room temperature The solution was transferred to a dropping funnel added dropwise to a flask After stirring overnight the mixture The organic layer was separated the solvent removed by vacuum

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL round bottom flask there was added 400 mL of dry tetrahydrofuran followed by 0.081 mole of HPPh2. The mixture was cooled to 0° C. and 0.081 mole of n-butyl lithium was slowly added to generate LiPPh2 ; this was slowly warmed to room temperature and stirred for about one hour. The solution was transferred to a dropping funnel and added dropwise to a flask containing 100 mL of 1,3-dichloropropane dissolved in 100 mL of diethyl ether. After stirring overnight the mixture was hydrolyzed with 25 mL of water. The organic layer was separated and the solvent removed by vacuum to leave Ph2P(CH2)3Cl that was stored under nitrogen until needed. this was slowly warmed to room temperature The solution was transferred to a dropping funnel added dropwise to a flask After stirring overnight the mixture The organic layer was separated the solvent removed by vacuum

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

Procedure: In a Schlenk flask were placed phenylphosphine (3.3806 g, 30.71 mmol) with THF (60 ml) and chilled to −30° C. in a freezer over 30 minutes. To this solution was added lithium diisopropylamide (16 ml, 32.16 mmol) and the resulting solution was allowed to warm to room temperature while stirring. In a 250 ml Schlenk flask was placed (C6H5)2P(CH2)3Cl (7.9089 g, 30.1 mmol) in 100 ml THF and the solution was cooled to −78° C. The lithium phenylphosphide solution was added to the (C6H5)2P(CH2)3Cl solution at such a rate that the temperature of the solution remained constant at −78° C. After addition, the solution was slowly warmed to room temperature. Degassed DI water (0.2 ml) was added to the dark orange solution. The color changed to yellow-orange. The solvents were removed in vacuo. The resulting gel was dissolved in toluene and filtered through Celite. Toluene was then removed in vacuo, leaving an orange-yellow oil. Yield: 10.0 g (99.1%). 31P{1H} NMR (CDCl3, 122 MHz, δppm: −16.30 and −52.86 (>99% pure). 1H NMR (CDCl3, 400 MHz, δ: 1.58–2.15 (3 complex peaks integrated to ˜7Hs), 4.12 (d of t, H—P) and 7.26–7.43 (complex pattern). In a Schlenk flask were placed In a 250 ml Schlenk flask was placed remained constant at −78° C After addition the solution was slowly warmed to room temperature The solvents were removed in vacuo The resulting gel was dissolved in toluene filtered through Celite Toluene was then removed in vacuo leaving an orange-yellow oil

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 500 mL round bottom flask there was added 400 mL of dry tetrahydrofuran followed by 0.081 mole of HPPh2. The mixture was cooled to 0° C. and 0.081 mole of n-butyl lithium was slowly added to generate LiPPh2 ; this was slowly warmed to room temperature and stirred for about one hour. The solution was transferred to a dropping funnel and added dropwise to a flask containing 100 mL of 1,3-dichloropropane dissolved in 100 mL of diethyl ether. After stirring overnight the mixture was hydrolyzed with 25 mL of water. The organic layer was separated and the solvent removed by vacuum to leave Ph2P(CH2)3Cl that was stored under nitrogen until needed. this was slowly warmed to room temperature The solution was transferred to a dropping funnel added dropwise to a flask After stirring overnight the mixture The organic layer was separated the solvent removed by vacuum