1-dioctylphosphoryloctane

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), BiCl3 (99.999%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.1M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 180° C. for 5 hr under inert atmosphere according to the procedure by Bullen et al.[42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al.[1]; a stock suspension of 2 mM BiCl3 in NMP was prepared in advance. 0.1M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), triphenylbismuth (99%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.2M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 200° C. for 2 hr under inert atmosphere according to the procedure by Bullen et al.[42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al.[1]; a stock suspension of 2 mM triphenylbismuth (BiPh3) in 1-octadecene was prepared in advance. 0.2M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), triphenylbismuth (99%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.2M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 200° C. for 2 hr under inert atmosphere according to the procedure by Bullen et al.[42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al.[1]; a stock suspension of 2 mM triphenylbismuth (BiPh3) in 1-octadecene was prepared in advance. 0.2M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), BiCl3 (99.999%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.1M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 180° C. for 5 hr under inert atmosphere according to the procedure by Bullen et al. [42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al. [1], a stock suspension of 2 mM BiCl3 in NMP was prepared in advance. 0.1M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), BiCl3 (99.999%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem) trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 1M TOP-Se was prepared by dissolving selenium powder in trioctylphosphine under inert atmosphere; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et. al.[1], a stock suspension of 2 mM BiCl3 in NMP was prepared in advance. 1M TOP-Se was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), BiCl3 (99.999%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem) trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 1M TOP-Se was prepared by dissolving selenium powder in trioctylphosphine under inert atmosphere; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et. al.[1], a stock suspension of 2 mM BiCl3 in NMP was prepared in advance. 1M TOP-Se was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Work up yielded trioctylphosphine oxide, a colourless solid FP 47.0° C., 365 g--75% yield on the octene used. a colourless solid FP 47.0° C., 365 g--75% yield

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

Procedure: A solution of 44.5 g of octyl chloride in 300 cc of xylene was added dropwise to 12 g of degreased and dry magnesium immersed in a few cc of anhydrous diethyl ether, whilst heating until the reaction started. When the reaction had started, the octyl chloride was added in the cold. When all the octyl chloride solution had been added, stirring was continued for about 1 hour further. 13.8 g of phosphorus oxychloride were then added in the cold. The mixture was then heated to boiling under reflux for 2 hours 30 minutes. The solution was hydrolysed by the addition of 1 litre of water acidified with 100 cc of HCl. The organic phase was decanted, washed with distilled water and neutralised with sodium bicarbonate. After decanting, the organic phase was recovered and then steam-distilled or steam-stripped to remove the solvent without distilling the product. A white solid, trioctylphosphine oxide, was obtained. whilst heating until the reaction The mixture was then heated under reflux for 2 hours 30 minutes The organic phase was decanted washed with distilled water and neutralised with sodium bicarbonate After decanting the organic phase was recovered steam-distilled steam-stripped to remove the solvent without distilling the product

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), BiCl3 (99.999%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.1M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 180° C. for 5 hr under inert atmosphere according to the procedure by Bullen et al.[42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al.[1]; a stock suspension of 2 mM BiCl3 in NMP was prepared in advance. 0.1M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), triphenylbismuth (99%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.2M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 200° C. for 2 hr under inert atmosphere according to the procedure by Bullen et al.[42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al.[1]; a stock suspension of 2 mM triphenylbismuth (BiPh3) in 1-octadecene was prepared in advance. 0.2M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), BiCl3 (99.999%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem), trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 0.1M Se-ODE was prepared by dissolving selenium powder in 1-octadecene at 180° C. for 5 hr under inert atmosphere according to the procedure by Bullen et al. [42]; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et al. [1], a stock suspension of 2 mM BiCl3 in NMP was prepared in advance. 0.1M Se-ODE was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance

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

Procedure: Materials. 1-methyl-2-pyrrolidinone (99.5%, Aldrich), 1-octadecene (90%, Aldrich), acetonitrile (99.9%, Fisher Chemical), BiCl3 (99.999%, Strem), CdO (99.5%, Aldrich), diphenyl ether (99%, Aldrich), methanol (ACS grade, VWR), oleic acid (90%, Aldrich), oleylamine (70% Aldrich), selenium (99.99%, Strem) trioctylphosphine (90%, Aldrich), trioctylphosphine oxide (99%, Strem), toluene (ACS grade, VWR). 1M TOP-Se was prepared by dissolving selenium powder in trioctylphosphine under inert atmosphere; trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile prior to use; di-n-octylphosphinic acid (DOPA) was synthesized according to the procedure reported by Wang et. al.[1], a stock suspension of 2 mM BiCl3 in NMP was prepared in advance. 1M TOP-Se was prepared trioctylphosphine oxide (TOPO) was recrystallized from acetonitrile was prepared in advance