dimethyl(phenyl)phosphane

Conditions: temp:255.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of decanoic acid (10.0 g, 0.0581 mol), acetic anhydride (5.93 g, 0.0581 mol), chlorodicarbonylrhodium (I) dimer (0.113 g, 2.9×10-4 mol), and dimethylphenylphosphine (0.16 g, 0.0012 mol) was heated under a slow stream of nitrogen using an oil bath maintained at 255° C. As product distilled from the reactor, it was continuously replaced with an equimolar mixture of decanoic acid and acetic anhydride, which also contained 0.6 mol % of dimethylphenylphosphine (relative to the decanoic acid content of the feed), in a rate that maintained the initial level of the reactor contents throughout the course of the entire reaction. The olefin product was removed as rapidly as possible from the reactor. The formation of product ceased after ca. 90 hours of reaction time. Examination of the combined distillate product by GC (using n-decane as an internal standard) showed the presence of 433 g of 1-nonene (isolated yield of 94% based on decanoic acid employed), which was found to be 99.2% of the α-olefin. TON=5915. was heated under a slow stream of nitrogen using an oil bath As product distilled from the reactor, it was continuously replaced with an equimolar mixture of decanoic acid and acetic anhydride, which also contained 0.6 mol % of dimethylphenylphosphine (relative to the decanoic acid content of the feed), in a rate that maintained the initial level of the reactor contents throughout the course of the entire reaction The olefin product was removed as rapidly as possible from the reactor The formation of product ceased after ca. 90 hours of reaction time

Conditions: temp:255.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a procedure similar to example 3, a mixture of stearic acid (70.0 g, 0.246 mol), propionic anhydride (16.0 g, 0.123 mol), chlorodicarbonylrhodium (I) dimer (0.48 g, 0.0012 mol), and dimethylphenylphosphine (0.68 g, 0.0049 mol) was heated under reduced pressure (35-45 torr) using an oil bath maintained at 255° C. and the product collected as it distilled from the reactor. The material removed from the reactor was continuously replaced with a mixture of stearic acid and propionic anhydride (4:3 molar mixture, respectively) in a rate that maintained the initial level of the reactor contents throughout the course of the entire reaction. The formation of product ceased after ca. 8 hours of reaction time. The combined distillate product was washed with water and distilled to provide 375 g of 1-heptadecene (bp 140° C./0.6 torr) which was found by GC analysis to be 93.4% of the α-olefin. TON=657. was heated under reduced pressure (35-45 torr) the product collected as it distilled from the reactor The material removed from the reactor was continuously replaced with a mixture of stearic acid and propionic anhydride (4 3 molar mixture, respectively) in a rate that maintained the initial level of the reactor contents throughout the course of the entire reaction The formation of product ceased after ca. 8 hours of reaction time The combined distillate product was washed with water distilled

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

Procedure: Pd(OAc)2 (3 mol %, 11 mg), PMe2Ph (5 mol %, 11 mg), 1-chloronaphthalen-2-yl trifluoromethanesulfonate (500 mg, 1.61 mmol), acrylonitrile (103 mg, 1.93 mmoli), triethylamine (242 mg, 2.4 mmol) and 15 mL of acetonitrile were added to a microvawe vial and the mixture was irradiated by MW at 120° C. for 1 h. At the conclusion of the reaction, the solvent was evaporated under reduced pressure and the residue was treated with dichloromethane and washed with water; the organic layer was filtered through a pad of silica gel with copious washings, concentrated, and purified by flash chromatography on silica gel eluted with petroleum ether/ethyl acetate (93:7) to give (2E)-3-(1-chloronaphthalen-2-yl)prop-2-enenitrile as colourless oil (120 mg, 35% yield). the mixture was irradiated by MW at 120° C. for 1 h At the conclusion of the reaction the solvent was evaporated under reduced pressure the residue was treated with dichloromethane washed with water the organic layer was filtered through a pad of silica gel with copious washings concentrated purified by flash chromatography on silica gel eluted with petroleum ether/ethyl acetate (93:7)